The photochemical total synthesis of(±)-3-OXO-α-cadinol and (±)-α-cadinol

✍ Scribed by Drury Caine; A. Stephen Frobese

• Book ID: 104235471
• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 284 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83172-5

✦ Synopsis

In a recently reported total synthesis of the sesquiterpene (f)-oplopanone (&) we utilized photochemical rearrangement of the 6/5-fused 4-methoxy dienone 3 to prepare the 5/6-fused acetoxy enone &which was readily transformed into the natural product. We now wish to report the total synthesis of the cadinane derivatives (f)-3-oxo-a-cadinol (&)3 4 and (f)-a-cadinol (&) by a sequence which utilizes photochemical rearrangement of the bicyclic dienone & in glacial acetic acid to produce the acetoxy enone & followed by expansion of the A ring.