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Stereocontrolled Second Generation Syntheses of the ABC and FG Ring Systems of Brevetoxin B

Year: 1990

Type: article

Abstract: Stereocontrolled, second generation syntheses 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.

Source: Tetrahedron

DOI: 10.1016/s0040-4020(01)85579-4

Authors: K.C. Nicolaou, D.A. Nugiel, E. Couladouros, C.-K. Hwang

Institutions: University of California San Diego, Scripps Clinic, University of Pennsylvania

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,680

OpenAlex ID: W1968026924

FWCI: 1.37

Cites: 25

Cited by: 101

Related to: 10