Total synthesis of papulacandin D

Tetsuya Kobayashi; Christopher S. Regens; Scott E. Denmark

doi:10.5059/yukigoseikyokaishi.66.616

Total synthesis of papulacandin D

Tetsuya Kobayashi, Christopher S. Regens, Scott E. Denmark

Chemistry

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

Abstract

A total synthesis of (+)-papulacandin D which shows an antifungal activity is reported. The molecule is one of the members of C-arylglycoside isolated from Papularia spherosperma. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the aryl glycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. This highly convergent synthesis was accomplished in 31 steps overall from commercial starting materials.

Original language	English (US)
Pages (from-to)	616-628
Number of pages	13
Journal	Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume	66
Issue number	6
DOIs	https://doi.org/10.5059/yukigoseikyokaishi.66.616
State	Published - Jun 2008

Keywords

Asymmetric allylation
C-arylglycoside
Cross-metathesis
Enantioselective lewis base catalysis
Organo-silanol cross-coupling reac-tion
Palladium
Papulacandin
Total synthesis

ASJC Scopus subject areas

Organic Chemistry

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10.5059/yukigoseikyokaishi.66.616

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title = "Total synthesis of papulacandin D",

abstract = "A total synthesis of (+)-papulacandin D which shows an antifungal activity is reported. The molecule is one of the members of C-arylglycoside isolated from Papularia spherosperma. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the aryl glycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. This highly convergent synthesis was accomplished in 31 steps overall from commercial starting materials.",

keywords = "Asymmetric allylation, C-arylglycoside, Cross-metathesis, Enantioselective lewis base catalysis, Organo-silanol cross-coupling reac-tion, Palladium, Papulacandin, Total synthesis",

author = "Tetsuya Kobayashi and Regens, {Christopher S.} and Denmark, {Scott E.}",

note = "Funding Information: Funding was provided by the National Institutes of Health (Grant R01 GM63167). CSR thanks Eli Lilly research laboratories and Johnson & Johnson PRI for graduate fellowships. We are also grateful to Prof. A. G. M. Barrett for providing spectra for synthetic (+)-papulacandin D.",

year = "2008",

month = jun,

doi = "10.5059/yukigoseikyokaishi.66.616",

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T1 - Total synthesis of papulacandin D

AU - Kobayashi, Tetsuya

AU - Regens, Christopher S.

AU - Denmark, Scott E.

N1 - Funding Information: Funding was provided by the National Institutes of Health (Grant R01 GM63167). CSR thanks Eli Lilly research laboratories and Johnson & Johnson PRI for graduate fellowships. We are also grateful to Prof. A. G. M. Barrett for providing spectra for synthetic (+)-papulacandin D.

PY - 2008/6

Y1 - 2008/6

N2 - A total synthesis of (+)-papulacandin D which shows an antifungal activity is reported. The molecule is one of the members of C-arylglycoside isolated from Papularia spherosperma. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the aryl glycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. This highly convergent synthesis was accomplished in 31 steps overall from commercial starting materials.

AB - A total synthesis of (+)-papulacandin D which shows an antifungal activity is reported. The molecule is one of the members of C-arylglycoside isolated from Papularia spherosperma. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the aryl glycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. This highly convergent synthesis was accomplished in 31 steps overall from commercial starting materials.

KW - Asymmetric allylation

KW - C-arylglycoside

KW - Cross-metathesis

KW - Enantioselective lewis base catalysis

KW - Organo-silanol cross-coupling reac-tion

KW - Palladium

KW - Papulacandin

KW - Total synthesis

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JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

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ER -

Total synthesis of papulacandin D

Abstract

Keywords

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