Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton

Ken Ichi Takao; Hiroyuki Yasui; Shun Yamamoto; Daisuke Sasaki; Soujiro Kawasaki; Gohshi Watanabe; Kin Ichi Tadano

doi:10.1021/jo048566j

Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton

Ken Ichi Takao, Hiroyuki Yasui, Shun Yamamoto, Daisuke Sasaki, Soujiro Kawasaki, Gohshi Watanabe, Kin Ichi Tadano

Department of Applied Chemistry

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

70 Citations (Scopus)

Abstract

The total syntheses of (+)-mycoepoxydiene and (-)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo-[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2- ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (-)-1893A was also synthesized via the vinylogous aldol reaction.

Original language	English
Pages (from-to)	8789-8795
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	69
Issue number	25
DOIs	https://doi.org/10.1021/jo048566j
Publication status	Published - 2004 Dec 10

ASJC Scopus subject areas

Organic Chemistry

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Takao, K. I., Yasui, H., Yamamoto, S., Sasaki, D., Kawasaki, S., Watanabe, G., & Tadano, K. I. (2004). Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton. Journal of Organic Chemistry, 69(25), 8789-8795. https://doi.org/10.1021/jo048566j

Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton. / Takao, Ken Ichi; Yasui, Hiroyuki; Yamamoto, Shun et al.
In: Journal of Organic Chemistry, Vol. 69, No. 25, 10.12.2004, p. 8789-8795.

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

Takao, KI, Yasui, H, Yamamoto, S, Sasaki, D, Kawasaki, S, Watanabe, G & Tadano, KI 2004, 'Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton', Journal of Organic Chemistry, vol. 69, no. 25, pp. 8789-8795. https://doi.org/10.1021/jo048566j

Takao KI, Yasui H, Yamamoto S, Sasaki D, Kawasaki S, Watanabe G et al. Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton. Journal of Organic Chemistry. 2004 Dec 10;69(25):8789-8795. doi: 10.1021/jo048566j

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title = "Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton",

abstract = "The total syntheses of (+)-mycoepoxydiene and (-)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo-[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2- ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (-)-1893A was also synthesized via the vinylogous aldol reaction.",

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AU - Takao, Ken Ichi

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AB - The total syntheses of (+)-mycoepoxydiene and (-)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo-[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2- ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (-)-1893A was also synthesized via the vinylogous aldol reaction.

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Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton

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