STUDIES DIRECTED TOWARD THE TOTAL SYNTHESIS OF TETRONOLIDE .1. AN ENANTIOSELECTIVE SYNTHESIS OF THE OCTAHYDRONAPHTHALENE UNIT

[摘要] An efficient enantioselective route to the octahydronaphthalene unit present in tetronolide (1), the stereochemically complex aglycone common to the tetrocarcins, a novel group of antitumor substances, is described. The sequence employs the intramolecular Diels-Alder reaction to control the relative stereochemistry present on the trans decalin ring system, and incorporates a masked acylating agent which should permit coupling of the two key fragments 2 and 3 as demonstrated by reaction of pentaene 4 with methanol and a model alpha-hydroxy ester.

[发布日期] 1991-08-12