Total synthesis of (−)-exiguolide via an organosilane-based strategy

2015 ◽  
Vol 51 (40) ◽  
pp. 8484-8487 ◽  
Author(s):  
Hongze Li ◽  
Hengmu Xie ◽  
Zhigao Zhang ◽  
Yongjin Xu ◽  
Ji Lu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Side Chain ◽  
Prins Cyclization ◽  
Key Steps

An organosilane-based strategy has been used to accomplish the total synthesis of (–)-exiguolide. The key steps involve: (1) geminal bis(silyl) Prins cyclization to construct the A ring; (2) silicon-protected RCM reaction to construct the macrocycle; and (3) Hiyama–Denmark cross-coupling to install the side chain.

scholarly journals Total Synthesis of Surinamensinols A and B

SynOpen ◽  
2020 ◽  
Vol 04 (04) ◽  
pp. 84-88
Author(s):  
Ahmed Al-Harrasi ◽  
Satya Kumar Avula ◽  
Biswanath Das ◽  
Rene Csuk ◽  
Ahmed Al-Rawahi
Keyword(s):  
Total Synthesis ◽  
Allyl Alcohol ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Ethyl Lactate ◽  
Naturally Occurring ◽  
Cross Coupling Reaction ◽  
Synthetic Sequence ◽  
Key Steps ◽  
Single Approach

AbstractAn efficient total synthesis of the naturally occurring anti-inflammatory and antitumour 8-O-4′-neolignans, surinamensinols A and B, has been accomplished from commercially available allyl alcohol and (S)-ethyl lactate. The synthetic sequence involves a palladium-catalysed Suzuki–Miyaura cross-coupling reaction followed by a chiral Mitsunobu­ reaction as the key steps. This is the first report of the simultaneous stereoselective total synthesis of surinamensinols A and B through a single approach involving only six steps.

Total synthesis of giffonin H by fluoride-catalyzed macrocyclization

2019 ◽  
Vol 6 (5) ◽  
pp. 704-708 ◽  
Author(s):  
Sooyoung Park ◽  
Seok-Ho Kim ◽  
Jin-Hyun Jeong ◽  
Dongyun Shin
Keyword(s):  
Total Synthesis ◽  
Cross Coupling ◽  
Synthetic Approach ◽  
Diaryl Ether ◽  
Key Steps ◽  
Highly Strained

First total synthesis of giffonin H, a highly strained 15-membered macrocyclic diaryl ether, has been achieved. Key steps include Ullmann cross coupling, (Z)-selective Julia–Kocienski olefination, and fluoride-mediated macrocyclization of TMS-alkyne and aldehyde. The strategy used for macrocyclization is an unprecedented and unique synthetic approach for cyclic diarylheptanoids.

Synthesis of (+/−) arthrographol

1991 ◽  
Vol 69 (12) ◽  
pp. 1909-1916 ◽  
Author(s):  
William A. Ayer ◽  
Peter A. Craw
Keyword(s):  
Total Synthesis ◽  
Key Words ◽  
Pinus Contorta ◽  
Lodgepole Pine ◽  
Single Step ◽  
Side Chain ◽  
Phenyl Sulfide ◽  
Blue Stain ◽  
Subsequent Elimination ◽  
Key Steps

A total synthesis of (+/−) arthrographol (1) in seven steps from vanillin is reported. Key steps in the synthesis are a single-step conversion of 5-allylvanillin (2) into the benzofuranmethanol 6, alkylation of the chloride 25 with the lithium anion of crotyl phenyl sulfide to give the sulfide 26, and formation of the 1(E),3(E)-1,3-pentadienyl side chain of arthrographol (1) via oxidation of the sulfide 26 and subsequent elimination of phenylsulfenic acid. The synthetic (+/−) arthrographol (1) inhibits the growth of Ophiostoma clavigerum (Robin.-Jeff. & Davids.) Harrington, the most pathogenic of the fungi associated with the blue stain disease of lodgepole pine (Pinus contorta Dougl. var latifolia Engelm.). Key words: arthographol, alkylation, 2-butenyl phenyl sulfide, polyketide.

Chemoenzymatic total synthesis of ent-neopinone and formal total synthesis of ent-codeinone from β-bromoethylbenzene*

2011 ◽  
Vol 89 (6) ◽  
pp. 709-729 ◽  
Author(s):  
Jan Duchek ◽  
T. Graeme Piercy ◽  
Jacqueline Gilmet ◽  
Tomas Hudlicky
Keyword(s):  
Total Synthesis ◽  
Heck Reaction ◽  
Aldol Condensation ◽  
Side Chain ◽  
Prins Reaction ◽  
Toluene Dioxygenase ◽  
E Coli ◽  
Key Steps ◽  
New Compounds ◽  
Stereogenic Center

Formal total synthesis of ent-codeinone and ent-codeine was accomplished via the total synthesis of ent-neopinone attained in 14 steps from β-bromoethylbenzene. The key steps included (i) enzymatic dihydroxylation of β-bromoethylbenzene with E. coli JM109 (pDTG601a), an organism that overexpresses toluene dioxygenase, (ii) a Heck reaction to establish C-13 stereogenic center, (iii) aldol condensation, and (iv) 1,6-conjugate addition of the ethylamino side chain to C-9. Several other modes of construction of the C-9 and C-14 centers were also investigated: Mannich cyclization, and aza-Prins reaction. The synthesis of ent-codeinone was formalized by intersecting Fukuyama’s recently published approach. Experimental and spectral data are provided for all new compounds.

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

A Short Synthesis of the Plant Alkaloid 4-Methyl-2,6-naphthyridine

2019 ◽  
Vol 16 (12) ◽  
pp. 931-934 ◽  
Author(s):  
Alexandra Kamlah ◽  
Franz Bracher
Keyword(s):  
Pyridine Ring ◽  
Cross Coupling ◽  
Antirrhinum Majus ◽  
New Synthesis ◽  
Short Synthesis ◽  
Regioselective Oxidation ◽  
Key Steps

: A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antirrhinum majus has been developed. Key steps are a regioselective oxidation of 3-bromo-4,5- dimethylpyridine to the corresponding 4-formyl derivative, and the annulation of the second pyridine ring by Suzuki-Miyaura cross-coupling using (E)-2-ethoxyvinylboronic acid pinacol ester as a masked acetaldehyde equivalent. This protocol gives the alkaloid in four steps starting from commercially available 3,4-dimethylpyridine in 15% overall yield. This annulation protocol should be useful for the synthesis of other condensed pyridines as well.

Concise Total Synthesis of Curvulone B

Synlett ◽  
2020 ◽  
Author(s):  
Debendra K. Mohapatra ◽  
Shivalal Banoth ◽  
Utkal Mani Choudhury ◽  
Kanakaraju Marumudi ◽  
Ajit C. Kunwar
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Ring System ◽  
Bond Forming ◽  
Cross Metathesis ◽  
Bond Forming Reactions ◽  
Key Steps

AbstractA concise and convergent stereoselective synthesis of curvulone B is described. The synthesis utilized a tandem isomerization followed by C–O and C–C bond-forming reactions following Mukaiyama-type aldol conditions for the construction of the trans-2,6-disubstituted dihydropyran ring system as the key steps. Other important features of this synthesis are a cross-metathesis, epimerization, and Friedel–Crafts acylation.

Concise total synthesis of honokiol via Kumada cross coupling

2014 ◽  
Vol 55 (31) ◽  
pp. 4295-4297 ◽  
Author(s):  
Jada Srinivas ◽  
Parvinder Pal Singh ◽  
Yogesh Kumar Varma ◽  
Irfan Hyder ◽  
Halmuthur M. Sampath Kumar
Keyword(s):  
Total Synthesis ◽  
Cross Coupling

ChemInform Abstract: Total Synthesis of a New 7-Deoxyidarubicinone Derivative Through the Functionalization of an A-Ring Side Chain.

ChemInform ◽  
2000 ◽  
Vol 31 (49) ◽  
pp. no-no
Author(s):  
Young S. Rho ◽  
Hyun Kyoung Ko ◽  
Wan-Joong Kim ◽  
Dong Jin Yoo ◽  
Heun Soo Kang
Keyword(s):  
Total Synthesis ◽  
Side Chain

First Total Synthesis of a Fluorinated Calystegin

2010 ◽  
Vol 65 (4) ◽  
pp. 445-451 ◽  
Author(s):  
René Csuk ◽  
Erik Prell ◽  
Stefan Reißmann ◽  
Claudia Korb
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Competitive Inhibitor ◽  
Ring Closure ◽  
Target Compound ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Ring Opening Reaction ◽  
Ultrasound Assisted ◽  
Key Steps

A straightforward chiral pool synthesis for the first fluorinated calystegin is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. The target compound is a selective and competitive inhibitor for a β -glycosidase.

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