Photochemistry of 1-acetoxy-2-(pent-4-enoyl)cyclopentenes: An efficient synthesis of 7-acetoxy-5-methyltricyclo(5.3.01,5)decan-2-one, a potential intermediate to pseudoguaiane ring.

doi:10.1248/CPB.32.3751

Paper

Photochemistry of 1-acetoxy-2-(pent-4-enoyl)cyclopentenes: An efficient synthesis of 7-acetoxy-5-methyltricyclo(5.3.01,5)decan-2-one, a potential intermediate to pseudoguaiane ring.

Published Sep 25, 1984 · H. Seto, Y. Fujimoto, H. Yoshioka

Chemical & Pharmaceutical Bulletin

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Abstract

The intramolecular photocycloadditions of 1-acetoxy-2-(pent-4-enoyl) cyclopentene (3a) and its analogues have been investigated. The 4'-methyl analogue (3b) afforded a straight adduct (4b) in 82.5% yield as a sole product, in contrast to the case for (3a) resulting in a mixture of the straight and cross adducts, (4a) and (5a), in a 1 : 1-1 : 8 ratio. On the other hand, 5', 5'-dimethyl analogue (3c) yielded the cross adduct (5c) together with a major product (6) due to a concurrent photo-ene reaction. The differences of regioselectivity due to the substitution pattern of the terminal double bond in (3) may be interpreted in terms of the preferential formation of corresponding exciplexes governed by non-bonding steric interactions.

Study Snapshot

The 4'-methyl analogue (3b) efficiently synthesized 7-acetoxy-5-methyltricyclo(5.3.01,5)decan-2-one, a potential intermediate for pseudoguaiane ring, with regioselectivity influenced by substitution patterns of the terminal double bond

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Photochemistry of 1-acetoxy-2-(pent-4-enoyl)cyclopentenes: An efficient synthesis of 7-acetoxy-5-methyltricyclo(5.3.01,5)decan-2-one, a potential intermediate to pseudoguaiane ring.

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