Total Synthesis Of The Antitumor Agent Asparagamine A

Christopher J Sinz
California Institute Of Technology
office Of Sponsored Research, Mail Code 201-15
pasadena, Ca 91125

Grant 1F32CA091635-01 from National Cancer Institute IRG: MCHA

Abstract: The goal of the proposed research is to develop an enantioselective synthesis of the antitumor alkaloid asparagamine A, which has been shown to have antitumor activity in vitro against a variety of tumor cell lines. MacMillan has recently developed the first organocatalytic, asymmetric Michael additions of pyrroles with alpha, beta- unsaturated aldehydes. Proposed herein is a novel extension to allow for the intervention of an aza-Prins cyclization of an iminium ion intermediate in the catalytic cycle. This will allow for a one-step synthesis of the core bridged pyrrolidine structure common to asparagamine A and stemofoline, a related alkaloid. The proposed synthesis is both novel and concise. Moreover, the proposed route will allow for the construction of analogs of the natural product that could be of significant medicinal value

Keywords: alkaloid, antineoplastic, drug design /synthesis /production chemical addition, cyclization, stereoisomer chemical synthesis, stereochemistry

1F32CA091635-01 (2001): $33260

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Total Synthesis Of The Antitumor Agent Asparagamine A

Christopher J Sinz
California Institute Of Technology
office Of Sponsored Research, Mail Code 201-15
pasadena, Ca 91125

Grant 5F32CA091635-02 from National Cancer Institute IRG: MCHA

Abstract: The goal of the proposed research is to develop an enantioselective synthesis of the antitumor alkaloid asparagamine A, which has been shown to have antitumor activity in vitro against a variety of tumor cell lines. MacMillan has recently developed the first organocatalytic, asymmetric Michael additions of pyrroles with alpha, beta- unsaturated aldehydes. Proposed herein is a novel extension to allow for the intervention of an aza-Prins cyclization of an iminium ion intermediate in the catalytic cycle. This will allow for a one-step synthesis of the core bridged pyrrolidine structure common to asparagamine A and stemofoline, a related alkaloid. The proposed synthesis is both novel and concise. Moreover, the proposed route will allow for the construction of analogs of the natural product that could be of significant medicinal value

Keywords: alkaloid, antineoplastic, drug design /synthesis /production chemical addition, cyclization, stereoisomer chemical synthesis, stereochemistry

Project start date: 2002-09-04

Project end date: 2003-07-15

5F32CA091635-02 (2002): $38320