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TOTAL SYNTHESES OF (+)-DIHYDROCOMPACTIN, (+)-COMPACTIN AND ANALOGS
Abstract
The mevinic acids are a structurally unique class of compounds which have shown to competitively inhibit 3-hydroxyl-3-methylglutaryl coenzyme A(HMG Co A) reductase, the rate-controlling enzyme in cholesterol biosynthesis. The total synthesis of two of these acids, (+)-dihydrocompactin (8) and compactin (7) is described. The key synthetic transformation involves addition of the dianion of sulfone 127 (for dihydrocompactin) or 128 (for compactin) to the lithium carboxylate of (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) (UNFORMATTED TABLE FOLLOWS) 7 R=H; (DELTA)('4a)'(',5)' Compactin (ML-236B) 127 4a, 5=(alpha)H 8 R=H; 4a', 5'=(alpha)H Dihydrocompactin 128 (DELTA)('4a,5) (TABLE ENDS) epoxy acid 130. The sulfone 127 is efficiently and stereospecifi- cally constructed from the Lewis acid mediated intramolecular Diels-Alder of optically enriched trienoate 131d. The epoxy acid 130, is prepared in optically pure form from L-malic acid. In addition, lactone synthons 129 and 221 and analogs 262, 264 and 266 were also synthesized. (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) (UNFORMATTED TABLE FOLLOWS) 262 R=H 264 266 (TABLE ENDS)
Subject Area
Organic chemistry
Recommended Citation
ZELLER, WAYNE EDWARD, "TOTAL SYNTHESES OF (+)-DIHYDROCOMPACTIN, (+)-COMPACTIN AND ANALOGS" (1985). ETD collection for University of Nebraska-Lincoln. AAI8526609.
https://digitalcommons.unl.edu/dissertations/AAI8526609