A New, Stereoselective Approach to the [3.3.3]Propellane System: Synthesis of (±)-modhephene. Preliminary communication

Von Oppolzer, Wolfgang; Marazza, Fabrizio

doi:10.1002/hlca.19810640537

Scientific article

English

A New, Stereoselective Approach to the [3.3.3]Propellane System: Synthesis of (±)-modhephene. Preliminary communication

ContributorsVon Oppolzer, Wolfgang; Marazza, Fabrizio

Published inHelvetica chimica acta, vol. 64, no. 5, p. 1575-1578

Publication date1981-07-22

First online date2004-10-25

Abstract

The unusual propellane skeleton of the sesquiterpene modhephene (1) has been synthesized starting from cyclopentenone (2). The key step 6 → 7 is an efficient and highly stereoselective intramolecular thermal ene-reaction. Further elaboration of the propellane 7 gave the enone 10 which had been previously converted to (±)-modhephene (1) in three steps.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, MARAZZA, Fabrizio. A New, Stereoselective Approach to the [3.3.3]Propellane System: Synthesis of (±)-modhephene. Preliminary communication. In: Helvetica chimica acta, 1981, vol. 64, n° 5, p. 1575–1578. doi: 10.1002/hlca.19810640537

Article (Published version)

Identifiers

PID : unige:169149
DOI : 10.1002/hlca.19810640537

Additional URL for this publicationhttps://onlinelibrary.wiley.com/doi/10.1002/hlca.19810640537

Journal ISSN0018-019X

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A New, Stereoselective Approach to the [3.3.3]Propellane System: Synthesis of (±)-modhephene. Preliminary communication

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