Total Synthesis of Natural Acetylenic Analogues of Isorenieratene and Renieratene

The total synthesis of two natural acetylenic aromatic carotenoids, 7,8-didehydroisorenieratene (1) and 7,8-didehydrorenieratene (2), was carried out. Although the condensations involving C15-acetylenic ylids (derived from the phosphonium salts 7, and 8) as the intermediates gave only 9-cis isomers...

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Published inBulletin of the Chemical Society of Japan Vol. 47; no. 2; pp. 350 - 354
Main Authors Ike, Tetsuji, Inanaga, Junji, Nakano, Akio, Okukado, Nobuhisa, Yamaguchi, Masaru
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.02.1974
Chemical Society of Japan
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Abstract The total synthesis of two natural acetylenic aromatic carotenoids, 7,8-didehydroisorenieratene (1) and 7,8-didehydrorenieratene (2), was carried out. Although the condensations involving C15-acetylenic ylids (derived from the phosphonium salts 7, and 8) as the intermediates gave only 9-cis isomers of 1 and 2, low-temperature condensations of C25-hexaene yield (derived from 19 and 28) with C15-acetylenic aldehyde (12a) led to all-trans 1 and 2, which were identical with natural specimens.
AbstractList The total synthesis of two natural acetylenic aromatic carotenoids, 7,8-didehydroisorenieratene (1) and 7,8-didehydrorenieratene (2), was carried out. Although the condensations involving C15-acetylenic ylids (derived from the phosphonium salts 7, and 8) as the intermediates gave only 9-cis isomers of 1 and 2, low-temperature condensations of C25-hexaene yield (derived from 19 and 28) with C15-acetylenic aldehyde (12a) led to all-trans 1 and 2, which were identical with natural specimens.
Abstract The total synthesis of two natural acetylenic aromatic carotenoids, 7,8-didehydroisorenieratene (1) and 7,8-didehydrorenieratene (2), was carried out. Although the condensations involving C15-acetylenic ylids (derived from the phosphonium salts 7, and 8) as the intermediates gave only 9-cis isomers of 1 and 2, low-temperature condensations of C25-hexaene yield (derived from 19 and 28) with C15-acetylenic aldehyde (12a) led to all-trans  1 and 2, which were identical with natural specimens.
Author Inanaga, Junji
Nakano, Akio
Ike, Tetsuji
Okukado, Nobuhisa
Yamaguchi, Masaru
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Snippet The total synthesis of two natural acetylenic aromatic carotenoids, 7,8-didehydroisorenieratene (1) and 7,8-didehydrorenieratene (2), was carried out. Although...
Abstract The total synthesis of two natural acetylenic aromatic carotenoids, 7,8-didehydroisorenieratene (1) and 7,8-didehydrorenieratene (2), was carried out....
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Title Total Synthesis of Natural Acetylenic Analogues of Isorenieratene and Renieratene
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