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  • Ring-closing metathesis/fragmentation route to geometrically defined medium-ring cycloalkenes: total synthesis of (+/-)-periplanone C.

Ring-closing metathesis/fragmentation route to geometrically defined medium-ring cycloalkenes: total synthesis of (+/-)-periplanone C.

Organic letters (2004-04-09)
Aleksandar Ivkovic, Radomir Matovic, Radomir N Saicic
ABSTRACT

The combination of alkene metathesis and beta-fragmentation offers an efficient entry into (Z)-configured medium-ring cycloalkenes. The versatility of this method is demonstrated by the total synthesis of Periplanone C, a semiochemical of Periplaneta americana. [reaction: see text]

MATERIALS
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Brand
Product Description

Sigma-Aldrich
3-Butenylmagnesium bromide solution, 0.5 M in THF