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Asymmetric Synthesis of (–)‐Pterosin N from a Chiral 1,3‐Dioxolanone
Author(s) -
Wu HsiuHan,
Hsu ShaoChien,
Hsu FengLin,
Uang BiingJiun
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402234
Subject(s) - chemistry , stille reaction , moiety , intramolecular force , stereoselectivity , enantioselective synthesis , total synthesis , aromatization , stereochemistry , diene , organic chemistry , catalysis , natural rubber
The first asymmetric total synthesis of (–)‐pterosin N from the N , N ‐diisopropyl‐10‐camphorsulfonamide‐derived chiral 1,3‐dioxolanone 11 has been accomplished in 9 steps with 8 % overall yield. The key steps in this synthesis were the highly stereoselective propargylation of 1,3‐dioxolanone 11 to construct the chiral tertiary alcohol moiety, construction of a diene‐ynone by Stille coupling, and an intramolecular Diels–Alder reaction followed by aromatization to finish the synthesis.