Work

Synthetic Studies Toward (−)-FR901483 Using a Conjugate Allylation To Install the C-1 Quaternary Carbon

Year: 2006

Type: article

Abstract: Two approaches to the aza-tricyclo dodecane skeleton of (-)-FR901483 are reported. Both routes utilized a Grignard addition to an N-acylpyridinium salt to establish the absolute stereochemistry at C-6 and a highly diastereoselective conjugate allylation reaction to form the quaternary center at C-1 of the natural product in an excellent yield. Although the desired polysubstituted piperidine intermediates were prepared regio- and stereoselectively, the construction of the C-8/C-9 bond connectivity could not be achieved. All attempts at a pinacol cyclization or an intramolecular 6-exo-tet epoxide opening were unsuccessful because of an unfavorable A(1,3) strain inherent in the molecule.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo061677t

Authors: Dimitar B. Gotchev, Daniel L. Comins

Institution: North Carolina State University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Wellcome Trust, National Institute of General Medical Sciences

Awards: SYNTHESIS AND SYNTHETIC UTILITY OF 1-ACYLDIHYDROPYRIDINE, G6559500453