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A Carbohydrate Approach for the First Total Synthesis of Cochliomycin C: Stereoselective Total Synthesis of Paecilomycin E, Paecilomycin F and 6′‐ epi ‐Cochliomycin C
Author(s) -
Mahankali Bakkolla,
Srihari Pabbaraja
Publication year - 2015
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.201500395
Subject(s) - total synthesis , chemistry , regioselectivity , ring closing metathesis , stereoselectivity , lactone , metathesis , stereochemistry , mitsunobu reaction , alkynylation , organic chemistry , natural product , catalysis , polymer , polymerization
Abstract The first total synthesis of the chlorinated resorcylic acid lactone cochliomycin C is achieved starting from the readily available sugar D ‐lyxose. The strategy has also lead to the total synthesis of natural resorcylic acid lactones paecilomycin E, paecilomycin F and a synthetic analogue 6‐ epi ‐cochliomycin C. The key reactions include Ohira–Bestmann alkynylation, ring closing metathesis and regioselective methylation under Mitsunobu conditions.