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Structural and Stereochemical Diversity from (±)‐2,2‐Dimethyl‐8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one − Application to the Synthesis of Polyketide Segments of Natural Products
Author(s) -
Vakalopoulos Alexandros,
Smits René,
Hoffmann H. Martin R.
Publication year - 2002
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 - 10.1002/1099-0690(200205)2002:9<1538::aid-ejoc1538>3.0.co;2-x
Subject(s) - chemistry , polyketide , stereochemistry , ring (chemistry) , organic chemistry , biosynthesis , enzyme
The racemic title compound has been transformed into both cyclic and acyclic segments of bioactive natural products, including the C10−C17 segment of pederin, the C12−C19 (C12′−C19′) segment of disorazole and the C1−C9 segment of auriside. A methodology for the opening of six‐membered ring acetals, containing gem ‐dimethyl groups, to δ‐hydroxy‐1,3‐dithianes has been developed. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)