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Enantioselective Synthesis of the Unsymmetrical Bis(lactone) (−)‐(3 E ,6 R ,9 E ,12 S ,14 R )‐Colletol Induced by Chiral Sulfoxides and an Approach to (+)‐Colletodiol by Asymmetric Hydroxylation of an α,β‐Hydroxy Lactone
Author(s) -
Solladié Guy,
Gressot Laurence,
Colobert Françoise
Publication year - 2000
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/(sici)1099-0690(200001)2000:2<357::aid-ejoc357>3.0.co;2-n
Subject(s) - chemistry , lactone , enantioselective synthesis , stereoselectivity , hydroxylation , stereochemistry , organic chemistry , catalysis , enzyme
Abstract A general synthetic strategy towards the two bis(lactones) (−)‐colletol ( 1 ) and (+)‐colletodiol ( 2 ) is described. A common intermediate in this synthesis is the 6‐membered hydroxy lactone (+)‐(3 R ,5 R )‐3‐hydroxy‐5‐hexanolide ( 6 ), readily prepared by stereoselective reduction of (+)‐( SR )‐methyl 3,5‐dioxo‐6‐( p ‐toluenesulfinyl)hexanoate ( 7 ). Stereoselective hydroxylation of this hydroxy lactone has allowed efficient access to (+)‐colletodiol ( 2 ).