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Enantioselective [2,3] wittig ring contraction induced by chiral bases. The total synthesis and absolute configuration of (+)-aristolactone

✍ Scribed by James A. Marshall; Jacques Lebreton

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
221 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Wittig ring contraction of the achiral 13-membered acetylenic ether 1 via treatment with lithio (R,R) or (S,S)-his-(1-phenylethyl)amide afforded the (RI-( +) or (S)-(-)-propargylic alcohol (+ J-2 or (-1-2, respectively, of >60% ee in 75% yield.

📜 SIMILAR VOLUMES

Enantioselective Total Synthesis and Abs
Enantioselective Total Synthesis and Absolute Configuration of the Natural Norsesquiterpene 7-Demethyl-2-methoxycalamenene by a Silane-Terminated Intramolecular Heck Reaction
✍ Tietze, Lutz F. ;Raschke, Thomas 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 English ⚖ 774 KB

## Abstract The total synthesis of the norsesquiterpene 7‐demethyl‐2‐methoxycalamenene (1) by a newly developed enantioselective silane‐terminated Heck reaction is described. The Pd^0^‐catalyzed transformation of the allylsilane 7, obtained from 3‐(3‐methoxyphenyl)propanol (2) in 7 steps, provides