Studies directed toward the total synthesis of tetronolide 1. An enantioselective synthesis of the octahydronaphthalene unit

✍ Scribed by Robert K. Boeckman Jr.; Thomas E. Barta; Scott G. Nelson

• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 259 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79871-6

✦ Synopsis

An efficfent enanboseieciwe route to the actahydronaphlhabne uaf preseni II) tetronollde (I), the stereochem~calty complex aglycone common to the telrocarcms, a novel group of anlilumor substances, IS described The sequence employs the mtramolecular D/e/s-Aider reaction to control the relatrve stereochem/strypresent on the trans decalm rmg system, and tncorporates a masked acyfahng agent which should permit couptmg of the two key fragments land 3 as demonstrated by react/on of pentaene 4 wth methanol and a mode/ a-hydroxy ester

The tetrocarcms comprise a group of antitumor antIbiotIc agents which share a comm0n aglycone, tetronolide 1 .i Structurally, tetronoltde IS reLtea't0 kljanoiia8 ana'ctilbrotlincolia'e, the aglpcone umfs of Illanomycin and'chlbrothncm, the onl) other known members ofthrs natural product