Asymmetric Total Synthesis of Caribenol A via an Intramolecular Diels–Alder Reaction

2013 ◽  
Vol 78 (11) ◽  
pp. 5492-5504 ◽  
Author(s):  
Jing-Chun Han ◽  
Lian-Zhu Liu ◽  
Yuan-Yuan Chang ◽  
Guo-Zong Yue ◽  
Jie Guo ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction

Catalytic Asymmetric Total Synthesis of (+)- and (−)-Paeoveitol via a Hetero-Diels–Alder Reaction

2017 ◽  
Vol 19 (3) ◽  
pp. 429-431 ◽  
Author(s):  
Tian-Ze Li ◽  
Chang-An Geng ◽  
Xiu-Juan Yin ◽  
Tong-Hua Yang ◽  
Xing-Long Chen ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Catalytic Asymmetric

Asymmetric Total Synthesis of (+)-Coprophilin

Synthesis ◽  
2017 ◽  
Vol 50 (06) ◽  
pp. 1301-1306 ◽  
Author(s):  
Isamu Shiina ◽  
Yuma Umezaki ◽  
Takatsugu Murata ◽  
Kyohei Suzuki ◽  
Takayuki Tonoi
Keyword(s):  
Total Synthesis ◽  
Aldol Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Core Structure ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Anticoccidial Agent

In this paper, we report the first total synthesis of (+)-coprophilin, an anticoccidial agent, by constructing the chiral linear precursor via a Mukaiyama–Evans aldol reaction and a stereoselective intramolecular Diels–Alder reaction. The proposed method can be used to provide large amounts of (+)-coprophilin, which exhibits a 3,4,5,6,7-pentasubstituted Δ1,2-octalin core structure.

An Asymmetric Total Synthesis of D-Homo Steroids Involving a Lewis Acid Directed Diels-Alder Reaction

1978 ◽  
Vol 8 (7) ◽  
pp. 427-436 ◽  
Author(s):  
Noal Cohen ◽  
Bruce L. Banner ◽  
Wayne F. Eichel ◽  
Zdenek Valenta ◽  
Robert A. Dickinson
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction

scholarly journals Divergent Asymmetric Total Synthesis of All Four Pestalotin Diastereomers from (R)-Glycidol

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 394 ◽  
Author(s):  
Mizuki Moriyama ◽  
Kohei Nakata ◽  
Tetsuya Fujiwara ◽  
Yoo Tanabe
Keyword(s):  
Total Synthesis ◽  
Lewis Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Aldol Reactions ◽  
Asymmetric Total Synthesis ◽  
High Chemical ◽  
Diels Alder Reaction ◽  
Mukaiyama Aldol ◽  
Optical Rotations

All four chiral pestalotin diastereomers were synthesized in a straightforward and divergent manner from common (R)-glycidol. Catalytic asymmetric Mukaiyama aldol reactions of readily-available bis(TMSO)diene (Chan’s diene) with (S)-2-benzyloxyhexanal derived from (R)-glycidol produced a syn-aldol adduct with high diastereoselectivity and enantioselectivity using a Ti(iOPr)4/(S)-BINOL/LiCl catalyst. Diastereoselective Mukaiyama aldol reactions mediated by catalytic achiral Lewis acids directly produced not only a (1′S,6S)-pyrone precursor via the syn-aldol adduct using TiCl4, but also (1′S,6R)-pyrone precursor via the antialdol adduct using ZrCl4, in a stereocomplementary manner. A Hetero-Diels-Alder reaction of similarly available mono(TMSO)diene (Brassard’s diene) with (S)-2-benzyloxyhexanal produced the (1′S,6S)-pyrone precursor promoted by Eu(fod)3 and the (1′S,6R)-pyrone precursor Et2AlCl. Debenzylation of the (1′S,6S)-precursor and the (1′S,6R)-precursor furnished natural (−)-pestalotin (99% ee, 7 steps) and unnatural (+)-epipestalotin (99% ee, 7 steps), respectively. Mitsunobu inversions of the obtained (−)-pestalotin and (+)-epipestalotin successfully produced the unnatural (+)-pestalotin (99% ee, 9 steps) and (−)-epipestalotin (99% ee, 9 steps), respectively, in a divergent manner. All four of the obtained chiral pestalotin diastereomers possessed high chemical and optical purities (optical rotations, 1H-NMR, 13C-NMR, and HPLC measurements).

Total synthesis of (−)-depyranoversicolamide B

2015 ◽  
Vol 51 (89) ◽  
pp. 16143-16146 ◽  
Author(s):  
Wen-Fang Qin ◽  
T. Xiao ◽  
D. Zhang ◽  
Lin-Feng Deng ◽  
Y. Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Key Steps

Asymmetric total synthesis of (−)-depyranoversicolamide B (12) is described from easily prepared chiral pyrroloindoline 21. Key steps in the synthesis are reductive ring opening of the pyrrolo ring in 21 and stereoselective intramolecular Diels–Alder reaction of 18.

Simple, efficient total synthesis of cantharidin via a high-pressure Diels-Alder reaction

1980 ◽  
Vol 102 (22) ◽  
pp. 6893-6894 ◽  
Author(s):  
William G. Dauben ◽  
Carl R. Kessel ◽  
Kazuo H. Takemura
Keyword(s):  
High Pressure ◽  
Total Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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