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Synthesis of a Tricyclic Core of Rameswaralide.

ABSTRACT: A tricyclic core containing a 5,7-fused bicyclic unit of rameswaralide was prepared starting from a 1,6-enyne. The synthetic sequence involved (i) ruthenium-catalyzed [5+2]-cycloaddition of 1,6-enyne, (ii) an acyl radical based approach to construct the lactone, and (iii) a regioselective installation of the conjugated double bond by a concomitant sulfenylation-dehydrosulfenylation sequence.

SUBMITTER: Trost BM

PROVIDER: S-EPMC2976576 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Synthesis of a Tricyclic Core of Rameswaralide.

Trost Barry M BM Nguyen Hien M HM Koradin Christopher C

Tetrahedron letters 20101201 48

A tricyclic core containing a 5,7-fused bicyclic unit of rameswaralide was prepared starting from a 1,6-enyne. The synthetic sequence involved (i) ruthenium-catalyzed [5+2]-cycloaddition of 1,6-enyne, (ii) an acyl radical based approach to construct the lactone, and (iii) a regioselective installation of the conjugated double bond by a concomitant sulfenylation-dehydrosulfenylation sequence. ...[more]

PMID: 21076637

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