Synthetic studies on spirovetivanes. I. Spirocondensation of a 4-(3′-formylpropyl)-3-cyclohexenone and stereospecific total synthesis of d1-β-vetivone.

✍ Scribed by Kiyoyuki Yamada; Hiroshi Nagase; Yoshihiro Hayakawa; Kozo Aoki; Yoshimasa Hirata

• Book ID: 104238716
• Publisher: Elsevier Science
• Year: 1973
• Tongue: French
• Weight: 249 KB
• Volume: 14
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)87385-8

✦ Synopsis

The structural feature of spirovetivanes,2 a group of sesquiterpenes is that they are the spiro[4.5]decane derivatives 1.

v

We have been interested in constructing the spiro[4.5]decane system generally suited for the synthesis of these sesquiterpenes.

We are reporting here a facile method of preparing the properly functionalized spiro[4.5] decane system by acid-catalyzed condensation of a 4-(3'-formylpropyl)-3-cyclohexenone derivative 2, and the stereospecific synthesis of B-vetivone 28, 3.