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Total Synthesis of Spirastrellolide A Methyl Ester—Part 2: Subunit Union and Completion of the Synthesis
Author(s) -
Paterson Ian,
Anderson Edward A.,
Dalby Stephen M.,
Lim Jong Ho,
Genovino Julien,
Maltas Philip,
Moessner Christian
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705566
Subject(s) - stannane , stille reaction , salt metathesis reaction , stereochemistry , metathesis , chemistry , key (lock) , total synthesis , computer science , organic chemistry , catalysis , operating system , polymerization , polymer
Succumbing to synthesis : The stereocontrolled total synthesis of spirastrellolide A methyl ester is reported. The union of two key C1–C16 and C17–C40 subunits is followed by macrolactonization and late‐stage side chain attachment by a cross‐metathesis reaction and a π‐allyl Stille coupling reaction with a C43–C47 stannane, thus confirming the 46 R configuration. The full configuration and conformation of the 38‐membered macrolide is revealed by single‐crystal X‐ray analysis of an advanced pentaol intermediate.