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Short Diastereoselective Synthesis of the C1–C13 (AB Spiroacetal) and C17–C28 Fragments (CD Spiroacetal) of Spongistatin 1 and 2 through Double Chain‐Elongation Reactions
Author(s) -
Flowers Christopher L.,
Vogel Pierre
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002204
Subject(s) - yield (engineering) , sequence (biology) , stereochemistry , chemistry , ring (chemistry) , enol , tetrahydropyran , physics , organic chemistry , catalysis , biochemistry , thermodynamics
A unique and practical synthetic sequence for rapid access to polyketides and to further the spiroacetals derived from them, which utilizes a bidirectional Hosomi–Sakurai allylation approach around key allylsilanes in the synthesis of the AB and CD ring systems of spongistatin 1 and 2, is reported. The synthesis of the AB spiroacetal 9 requires 13 steps, with a longest linear sequence of seven steps in an overall yield of 27 %. The synthesis of the CD spiroacetal 13 requires 15 steps, with a longest linear sequence of 11 steps in an overall yield of 30 %. Both syntheses start from but‐3‐enol.