Stereospecific synthesis of the C(3)-C(10) segment of aplasmomycin from (R)-pulegone

✍ Scribed by James D. White; Shen-chun Kuo; Thalathani R. Vedananda

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 171 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96285-3

✦ Synopsis

Sumnary:

A key subunit of aplasmomycin comprising C3-Cl0 of the syrnnetrical macrodiolide structure has been synthesized in optically pure form by two routes from (RI-(+I-pulegone. A strategic intermediate in our recent total synthesis of aplasmomycin (111 was the S-lactone 2, which provided the C(3)-C(10) segment in each half of the macrodiolide. Lactone 2 was prepared in racemic form via condensation of the dianion of tiglic acid with the monoacetal of 2,2-dimethylmalondialdehyde.2 The mixture of diastereomeric ortholactones obtained