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An expedient total synthesis of (±)-caparratriene

✍ Scribed by James R. Vyvyan; Emily A. Peterson; Mari L. Stephan

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
144 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

_)-Caparratriene has been synthesized by two succinct routes. The first relies on two Wittig reactions and produces (_)-caparratriene and its 2Z isomer as an inseparable 2:1 mixture. The second more efficient synthesis produces only the naturally occurring 2E isomer and proceeds in 36% overall yield. The key step in this short synthesis is the Suzuki coupling of E-2-bromo-2-butene with the E-vinyl borane derived from 4,8-dimethyl-7nonen-l-yne.

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✍ J. LI; Z. LIU; J. LAN; Y. LI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 2 views

First Total Synthesis of (+)-Caparratriene. -The title compound (V), a new sesquiterpene hydrocarbon with significant growth-inhibitory activity against CEM leukemia cells, is synthesized from commercially available citronellal (I) via three steps in an overall yield of 18%. Coupling reagent (II) i