ORGN 477 |
A reiterative epoxide-based approach toward the synthesis of the polypropionate chain of streptovaricin D
| Wildeliz Torres and Jose A. Prieto. Department of Chemistry, University of Puerto Rico, PO Box 23346, San Juan, PR 00931-3346 |
Streptovaricins are an important class of ansamycin antibiotics that are known to inhibit reverse transcriptase. Streptovaricin D consists of a naphtoquinone core and a polypropionate ansa chain with nine contiguous chiral centers. This compound represents an excellent, but demanding, target for applying the oxirane-based reiterative approach for polypropionate synthesis developed in our laboratory. The alkynyl alane mediated epoxide ring opening is a crucial step in this approach. In this way, 3,4-epoxy alcohols are efficiently transformed to the corresponding 1,3-diols. In addition, streptovaricin D requires the challenging introduction of a C10 carbomethoxy moiety. In order to demonstrate the generality of our methodology for polypropionate construction, we undertook this interesting endeavor. The construction of fragment C5-C10 of streptovaricin D ansa chain was performed in nine synthetic steps. The details of this study will be presented. Work supported by NIH RISE (1R25-GM-61151-01A1) and NIH SCORE (2S06GM-08102-29). |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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