Synthesis of dimethyl gloiosiphone A by way of palladium-catalyzed domino cyclization

Takayuki Doi; Yusuke Iijima; Masaru Takasaki; Takashi Takahashi

doi:10.1021/jo062546v

Synthesis of dimethyl gloiosiphone A by way of palladium-catalyzed domino cyclization

Takayuki Doi, Yusuke Iijima, Masaru Takasaki, Takashi Takahashi

PHA - Molecular Pharmaceutical Science

Tokyo Institute of Technology

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

(Chemical Equation Presented) The synthesis of a spiro[4.4]nonane skeleton by the palladium-catalyzed domino cyclization of a linear 7-methylene-2,10- undecadienyl acetate is described. The π-allylpalladium intermediate underwent intramolecular alkene insertion with high intraannular diastereoselectivity, followed by intramolecular Heck-type cyclization, leading to a spiro[4.4]nonane system. Oxidation of the allylic ether moiety and transformation of the vinyl group to an exo-methylene unit provided 3, which is the known synthetic intermediate of dimethyl gloiosiphone A (2).

Original language	English
Pages (from-to)	3667-3671
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	72
Issue number	10
DOIs	https://doi.org/10.1021/jo062546v
Publication status	Published - 2007 May 11

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abstract = "(Chemical Equation Presented) The synthesis of a spiro[4.4]nonane skeleton by the palladium-catalyzed domino cyclization of a linear 7-methylene-2,10- undecadienyl acetate is described. The π-allylpalladium intermediate underwent intramolecular alkene insertion with high intraannular diastereoselectivity, followed by intramolecular Heck-type cyclization, leading to a spiro[4.4]nonane system. Oxidation of the allylic ether moiety and transformation of the vinyl group to an exo-methylene unit provided 3, which is the known synthetic intermediate of dimethyl gloiosiphone A (2).",

author = "Takayuki Doi and Yusuke Iijima and Masaru Takasaki and Takashi Takahashi",

year = "2007",

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doi = "10.1021/jo062546v",

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T1 - Synthesis of dimethyl gloiosiphone A by way of palladium-catalyzed domino cyclization

AU - Doi, Takayuki

AU - Iijima, Yusuke

AU - Takasaki, Masaru

AU - Takahashi, Takashi

PY - 2007/5/11

Y1 - 2007/5/11

N2 - (Chemical Equation Presented) The synthesis of a spiro[4.4]nonane skeleton by the palladium-catalyzed domino cyclization of a linear 7-methylene-2,10- undecadienyl acetate is described. The π-allylpalladium intermediate underwent intramolecular alkene insertion with high intraannular diastereoselectivity, followed by intramolecular Heck-type cyclization, leading to a spiro[4.4]nonane system. Oxidation of the allylic ether moiety and transformation of the vinyl group to an exo-methylene unit provided 3, which is the known synthetic intermediate of dimethyl gloiosiphone A (2).

AB - (Chemical Equation Presented) The synthesis of a spiro[4.4]nonane skeleton by the palladium-catalyzed domino cyclization of a linear 7-methylene-2,10- undecadienyl acetate is described. The π-allylpalladium intermediate underwent intramolecular alkene insertion with high intraannular diastereoselectivity, followed by intramolecular Heck-type cyclization, leading to a spiro[4.4]nonane system. Oxidation of the allylic ether moiety and transformation of the vinyl group to an exo-methylene unit provided 3, which is the known synthetic intermediate of dimethyl gloiosiphone A (2).

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Synthesis of dimethyl gloiosiphone A by way of palladium-catalyzed domino cyclization

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