STEREOCONTROLLED 2ND GENERATION SYNTHESES OF THE ABC AND FG RING-SYSTEMS OF BREVETOXIN-B

Stereocontrolled, second generation synthesis of the ABC and FG ring systems of brevetoxin B (1) are described. The two key intermediates 2 and 3, representing the ABC and FG ring frameworks, were prepared from 2-deoxy-D-ribose via short and efficient sequences. The synthesis of 2 proceeded via the...

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Bibliographic Details
Published inTetrahedron Vol. 46; no. 13-14; pp. 4517 - 4552
Main Authors NICOLAOU, KC, NUGIEL, DA, COULADOUROS, E, HWANG, CK
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.1990
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:Stereocontrolled, second generation synthesis of the ABC and FG ring systems of brevetoxin B (1) are described. The two key intermediates 2 and 3, representing the ABC and FG ring frameworks, were prepared from 2-deoxy-D-ribose via short and efficient sequences. The synthesis of 2 proceeded via the epoxy alcohol cyclization precursors 6 and 7, and the Horner-Emmons cyclization precursor 5, to give the desired tricyclic system in 3.6% overall yield. The synthesis of 3 proceeded via the epoxy alcohol cyclization precursors 10 and 11 to give the desired bicyclic system in a 11.5% overall yield. Both syntheses represent improvements over the previous procedures and allow for rapid and facile entries into the ABC and FG ring systems of this complex natural product.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)85579-4