A Stereoselective Synthesis of (3E,5Z)-3,5-Tetradecadienoic Acid (Megatomoic Acid), the Sex Attractant of the Black Carpet Beetle

DOI: 10.1246/bcsj.56.3521

Source and publish data:

Bulletin of the Chemical Society of Japan p. 3521 - 3522 (1983)

Update date:2022-08-16

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Authors:

Tsuboi, Sadao

Masuda, Toshihide

Takeda, Akira

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Article abstract of DOI:10.1246/bcsj.56.3521

The total synthesis of (3E,5Z)-3,5-tetradecadienoic acid (megatomoic acid) is accomplished with 74percent stereoselectivity through the use of stereoselective rearrangement of ethyl 3,4-tridecadienoate to ethyl (2E,4Z)-2,4-tridecadienoate with alumina and the extension of the carbon chain with methyl methylthiomethyl sulfone.

Full text of DOI:10.1246/bcsj.56.3521

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