A Novel, Stereospecific Total Synthesis of (±)-δ9(12)-Capnellene from p-Cresol. -The novel synthesis of racemic capnellene (VI) is based on an inverse electron demand Diels-Alder reaction of a cyclohexadienone derived from (I) with cyclopentadiene (II) and an oxa-di-π-methane rearrangement of (IV).
✦ LIBER ✦
A novel, stereospecific total synthesis of (±)-Δ9(12)-capnellene from p-cresol
✍ Scribed by Vishwakarma Singh; S. Prathap; M. Porinchu
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 207 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A novel, efficient and stefeosp~ific synthesis of(_+) capnellene fi'om p-ca-esol is reported.
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## Abstract The synthesis of the (±)‐form of the marine sesquiterpene (–)‐Δ^9(12)^‐capnellene (**1**) by double application of the __a__‐alkynone cyclization is described. Starting with 2, 2, 5‐trim ethylcyclopentanone (**2**), the elaboration of the tricyclo [6.3.0.0^2,6^]undecane C‐skeleton of **