Stereocontrolled total synthesis of the triquinane marine sesquiterpene Δ9(12)-capnellene

1984 ◽  
Vol 62 (11) ◽  
pp. 2415-2420 ◽  
Author(s):  
Leo A. Paquette ◽  
Kenneth E. Stevens
Keyword(s):  
Total Synthesis ◽  
Nazarov Cyclization ◽  
Marine Origin ◽  
Steric Factors ◽  
Chiral Centers

A total synthesis of Δ9(12)-capnellene, a cis-anti-cis-tricyclo[6.3.0.02,6]undecane sesquiterpene of marine origin, is described. Starting with bicyclic enone 5, which was prepared by a Nazarov cyclization, the remaining portion of the molecule is elaborated by means of a new and relatively efficient cyclopentenone annulation scheme. The relative stereochemistries of the chiral centers are properly incorporated by taking advantage of prevailing steric factors.

Total Synthesis of Resolvin T4

Synlett ◽  
2021 ◽  
Author(s):  
Narihito Ogawa ◽  
Kohei Arai ◽  
Yuichi Kobayashi
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Transfer Hydrogenation ◽  
Asymmetric Transfer Hydrogenation ◽  
Ring Opening Reaction ◽  
Propargylic Alcohol ◽  
Chiral Centers ◽  
Wittig Reactions

AbstractA total synthesis of resolvin T4 was achieved by connecting three intermediates by Wittig reactions. The enal in the C1–C10 part was constructed through reduction of a propargylic alcohol with Red-Al followed by oxidation. The enal moiety in the C11–C16 part was synthesized by a ring-opening reaction of a silyl epoxide followed by a Peterson elimination. The chiral centers at C7 and C13 were constructed by ruthenium-catalyzed asymmetric transfer hydrogenation.

scholarly journals Total Synthesis of (±)-Rocaglamide via Oxidation-Initiated Nazarov Cyclization

2012 ◽  
Vol 77 (4) ◽  
pp. 1891-1908 ◽  
Author(s):  
John A. Malona ◽  
Kevin Cariou ◽  
William T. Spencer ◽  
Alison J. Frontier
Keyword(s):  
Total Synthesis ◽  
Nazarov Cyclization

Aplyronine A, a Potent Antitumor Substance of Marine Origin, Aplyronines B and C, and Artificial Analogues:  Total Synthesis and Structure−Cytotoxicity Relationships

1996 ◽  
Vol 61 (16) ◽  
pp. 5326-5351 ◽  
Author(s):  
Hideo Kigoshi ◽  
Kiyotake Suenaga ◽  
Tsuyoshi Mutou ◽  
Takeshi Ishigaki ◽  
Toshiyuki Atsumi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Marine Origin ◽  
Aplyronine A

ChemInform Abstract: THE USE OF A VERSATILE BUILDING BLOCK HAVING TWO CHIRAL CENTERS. A TOTAL SYNTHESIS OF (-)-OUDEMANSIN

1984 ◽  
Vol 15 (36) ◽  
Author(s):  
H. AKITA ◽  
H. KOSHIJI ◽  
A. FURUICHI ◽  
K. HORIKOSHI ◽  
T. OISHI
Keyword(s):  
Total Synthesis ◽  
Building Block ◽  
Chiral Centers

Asymmetric Total Synthesis of 16-Methyleicos-(4E )-en-1-yn-3-ol from the Marine Sponge Cribrochalina vasculum : Establishment of Absolute Configuration of Chiral Centers

2019 ◽  
Vol 4 (1) ◽  
pp. 399-402 ◽  
Author(s):  
Narayana Rao Gundoju ◽  
Ramesh Bokam ◽  
Nageswara Rao Yalavarthi ◽  
Karimulla Shaik ◽  
Mangala Gowri Ponnapalli
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Marine Sponge ◽  
Asymmetric Total Synthesis ◽  
Chiral Centers

scholarly journals Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

2020 ◽  
Vol 16 ◽  
pp. 670-673
Author(s):  
Jan Geldsetzer ◽  
Markus Kalesse
Keyword(s):  
Total Synthesis ◽  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Vinyl Bromide ◽  
Type Coupling ◽  
Chiral Centers

The stereoselective synthesis of the (Z)-enamide fragment of chondrochloren (1) is described. A Buchwald-type coupling between amide 3 and (Z)-bromide 4 was used to generate the required fragment. The employed amide 3 comprising three chiral centers was obtained through a seven-step sequence starting from ᴅ-ribonic acid-1,4-lactone. The (Z)-vinyl bromide 4 is accessible in four steps from 4-hydroxybenzaldehyde. The pivotal cross coupling between both fragments was achieved after extensive experimentation with copper(I) iodide, K2CO3 and N,N′-dimethylethane-1,2-diamine.

scholarly journals Total Synthesis of (.+-.)-Merrilactone A via Catalytic Nazarov Cyclization.

ChemInform ◽  
2007 ◽  
Vol 38 (24) ◽  
Author(s):  
Wei He ◽  
Jie Huang ◽  
Xiufeng Sun ◽  
Alison J. Frontier
Keyword(s):  
Total Synthesis ◽  
Nazarov Cyclization ◽  
Merrilactone A
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