Total synthesis of natural quadrone

1988 ◽  
Vol 66 (3) ◽  
pp. 528-530 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Montse Llinas-Brunet
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Efficient Synthesis ◽  
Camphorsulfonic Acid ◽  
Natural Form

Starting from the ammonium salt of (–)-10-camphorsulfonic acid (4), an efficient synthesis of quadrone (1) in natural form has been accomplished.

scholarly journals The total synthesis of D-chalcose and its C-3 epimer

2013 ◽  
Vol 9 ◽  
pp. 2620-2624 ◽  
Author(s):  
Jun Sun ◽  
Song Fan ◽  
Zhan Wang ◽  
Guoning Zhang ◽  
Kai Bao ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Grignard Reaction ◽  
Efficient Synthesis ◽  
Camphorsulfonic Acid ◽  
Asymmetric Dihydroxylation ◽  
Key Steps ◽  
Stereogenic Center ◽  
Hydroxy Groups

We completed a new and efficient synthesis of D-chalcose (I) and the first synthesis of its C-3 epimer (I′) in nine steps with overall yields of 23% and 24%, respectively. The key steps in the sequence were the formation of the stereocenter on C3 via Grignard reaction, the introduction of the stereogenic center on C2 by Sharpless asymmetric dihydroxylation, the protection of the C1 and C2 hydroxy groups with tert-butyldimethylsilyl trifluoromethanesulfonate (TBSOTf), and the selective cleavage of the primary OTBS ether using catalytic DL-10-camphorsulfonic acid (CSA) in MeOH.

Total synthesis of zizaane sesquiterpenes: (−)-khusimone, (+)-zizanoic acid, and (−)-epizizanoic acid

1982 ◽  
Vol 60 (9) ◽  
pp. 1081-1091 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Wing Hong Chan
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Active Form ◽  
Optically Active ◽  
Camphorsulfonic Acid

Three sesquiterpenes of the zizaane family, khusimone (1), epizizanoic acid (3), and zizanoic acid (2) have been synthesized in optically active form from the ammonium salt of (−)-l-10-camphorsulfonic acid in sixteen, nineteen, and twenty steps respectively.

A total synthesis of (−)-khusimone

1979 ◽  
Vol 57 (6) ◽  
pp. 708-709 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Wing Hong Chan
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Camphorsulfonic Acid

A total synthesis of (−)-khusimone (1), an odoriferous norsesquiterpenoid ketone, has been achieved in 16 steps from the ammonium salt of l-10-camphorsulfonic acid.

Synthesis of 14-hydroxy steroids. Total synthesis of methyl 14β-hydroxy-1,7,17-trioxo-5β,8-androstene-10β-oate and related compounds

1990 ◽  
Vol 68 (11) ◽  
pp. 1917-1922 ◽  
Author(s):  
Réjean Ruel ◽  
Pierre Deslongchamps
Keyword(s):  
Total Synthesis ◽  
Ammonium Salt ◽  
Michael Addition ◽  
Title Compound ◽  
Steroid Synthesis ◽  
Related Compounds ◽  
Acetylenic Ketone

The total synthesis of the title compound 22 and methyl 14α-hydroxy-5β,13α,8-androstene-1,7,17-trioxo-10β-oate 21 isomer is reported. We also describe the 1,6-Michael addition of 2-methyl-1,3-cyclopentanedione on dienone 14 and the protic ammonium salt catalyzed intramolecular Michael addition of cyclic β-ketoester on the conjugated acetylenic ketone 13. Keywords: cardenolides, steroid synthesis, aldol, Michael addition.

Toward the Total Synthesis of Phorboxazole B (II): An Efficient Synthesis of the C20?C46 Segment (I).

ChemInform ◽  
2005 ◽  
Vol 36 (12) ◽  
Author(s):  
De Run Li ◽  
Cai Yun Sun ◽  
Ce Su ◽  
Guo-Qiang Lin ◽  
Wei-Shan Zhou
Keyword(s):  
Total Synthesis ◽  
Efficient Synthesis ◽  
Phorboxazole B

Total synthesis of (+)-herboxidiene/GEX 1A

2017 ◽  
Vol 15 (8) ◽  
pp. 1842-1862 ◽  
Author(s):  
Alejandro Gómez-Palomino ◽  
Miquel Pellicena ◽  
Katrina Krämer ◽  
Pedro Romea ◽  
Fèlix Urpí ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Aldol Reactions ◽  
Efficient Synthesis

An efficient synthesis of herboxidiene is granted from highly stereoselective aldol reactions from two lactate-derived ketones and an oxa-Michael cyclization.

scholarly journals A Concise and Efficient Total Synthesis of α-Mangostin and β-Mangostin from Garcinia Mangostana

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800
Author(s):  
Dandan Xu ◽  
Ying Nie ◽  
Xizhou Liang ◽  
Ling Ji ◽  
Songyuan Hu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Claisen Rearrangement ◽  
Practical Approach ◽  
Efficient Synthesis ◽  
Garcinia Mangostana ◽  
Diverse Groups

The concise, efficient synthesis of α-mangostin is described in eight simple steps with 8.3% overall yield. Highlights include a practical approach to construct the isopentene groups and other diverse groups at C–2 and C–8 of the xanthene skeleton through Claisen rearrangement and Wittig reaction. Meanwhile the first total synthesis of β-mangostin is presented with a similar approach.

scholarly journals Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy

2013 ◽  
Vol 9 ◽  
pp. 983-990 ◽  
Author(s):  
Huili Liu ◽  
Kuan Zheng ◽  
Xiang Lu ◽  
Xiaoxia Wang ◽  
Ran Hong
Keyword(s):  
Total Synthesis ◽  
Synthetic Approach ◽  
Efficient Synthesis

A “stop-and-flow” strategy was developed for the chemoselective dioxygenation of alkenes with a PIFA-initiated cyclization. This method is conceived for the desymmetrization of seco-diene, and a series of substituted 5-hydroxymethyl-γ-lactones were constructed after hydrolysis. This strategy also differentiates terminally substituted alkenes and constitutes a potentially novel synthetic approach for the efficient synthesis toward velbanamine.

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