Total synthesis of halicholactone and neohalicholactone

The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using t...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 62; no. 19; pp. 6638 - 6657
Main Authors Critcher, DJ, Connolly, S, Wills, M
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 19.09.1997
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALGA CONSTANTINEA-SIMPLEX
DIASTEREOSELECTIVE SYNTHESIS
HALICHONDRIA-OKADAI KADOTA
ASYMMETRICALLY CATALYZED MACROCYCLIZATION
COUPLING REACTION
PROPARGYLIC ALCOHOLS
FATTY-ACID METABOLITES
CHIRAL BUILDING BLOCK
CORAL PLEXAURA-HOMOMALLA
C-H INSERTION
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Summary:The total synthesis of the marine natural products neohalicholactone (1) and halicholactone (2), in enantiomerically pure form, are reported. Key steps in the synthesis of each compound include a cis-selective Wittig reaction, stereoselective cyclopropanation, nine-membered lactone formation using the Yamaguchi method and late-stage stereoselective Cr(II)/Ni(II) mediated coupling of vinyl iodides 39 and 50 with aldehyde 14. In the case of the neohalicholactone synthesis the two major components which were coupled in this convergent synthesis were each derived from the enantiomers of commercially available malic acid. The synthesis served to confirm the original assignment of absolute configuration which was made by Yamada and Clardy. We also demonstrated, through the preparation of diastereoisomers, that another reported compound closely related to neohalicholactone is likely to be the C-15 epimer 67.
ISSN:0022-3263
DOI:10.1021/jo962312j