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Stereoselective Total Synthesis of (11 β )‐11‐Methoxycurvularin
Author(s) -
Rajesh Karuturi,
Suresh Vangaru,
Selvam Jondoss Jon Paul,
Babu Dokuburra Chanti,
Venkateswarlu Yenamandra
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900136
Subject(s) - chemistry , regioselectivity , stereoselectivity , intramolecular force , polyketide , acylation , natural product , friedel–crafts reaction , total synthesis , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biosynthesis , enzyme
A simple and highly efficient stereoselective total synthesis of (11 β )‐11‐methoxycurvularin ( 5 ), a polyketide natural product, was achieved. The synthesis commenced with a Cu‐mediated regioselective opening of (2 S )‐2‐methyloxirane ( 6 ) and comprised a Keck asymmetric allylation and intramolecular Friedel–Crafts acylation as key steps ( Scheme 2 ).