Total Synthesis of Discorhabdin C: A General Aza Spiro Dienone Formation from O-Silylated Phenol Derivatives Using a Hypervalent Iodine Reagent

Yasuyuki Kita; Hirofumi Tohma; Masanao Inagaki; Kenji Hatanaka; Takayuki Yakura

doi:10.1021/ja00032a036

Total Synthesis of Discorhabdin C: A General Aza Spiro Dienone Formation from O-Silylated Phenol Derivatives Using a Hypervalent Iodine Reagent

Yasuyuki Kita, Hirofumi Tohma, Masanao Inagaki, Kenji Hatanaka, Takayuki Yakura^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

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

196 Scopus citations

Abstract

Hypervalent iodine oxidation of O-silylated phenols bearing various types of aminoquinones at the para position in 2,2,2-trifluoroethanol gave azacarbocyclic spiro dienones in good yields. Using this method, the first total synthesis of discorhabdin C, which was isolated from the sponge of Latrunculia du Bocage in New Zealand, was achieved.

Original language	English
Pages (from-to)	2175-2180
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	114
Issue number	6
DOIs	https://doi.org/10.1021/ja00032a036
State	Published - 1992/03/01

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Total Synthesis of Discorhabdin C: A General Aza Spiro Dienone Formation from O-Silylated Phenol Derivatives Using a Hypervalent Iodine Reagent",

abstract = "Hypervalent iodine oxidation of O-silylated phenols bearing various types of aminoquinones at the para position in 2,2,2-trifluoroethanol gave azacarbocyclic spiro dienones in good yields. Using this method, the first total synthesis of discorhabdin C, which was isolated from the sponge of Latrunculia du Bocage in New Zealand, was achieved.",

author = "Yasuyuki Kita and Hirofumi Tohma and Masanao Inagaki and Kenji Hatanaka and Takayuki Yakura",

year = "1992",

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T2 - A General Aza Spiro Dienone Formation from O-Silylated Phenol Derivatives Using a Hypervalent Iodine Reagent

AU - Kita, Yasuyuki

AU - Tohma, Hirofumi

AU - Inagaki, Masanao

AU - Hatanaka, Kenji

AU - Yakura, Takayuki

PY - 1992/3/1

Y1 - 1992/3/1

N2 - Hypervalent iodine oxidation of O-silylated phenols bearing various types of aminoquinones at the para position in 2,2,2-trifluoroethanol gave azacarbocyclic spiro dienones in good yields. Using this method, the first total synthesis of discorhabdin C, which was isolated from the sponge of Latrunculia du Bocage in New Zealand, was achieved.

AB - Hypervalent iodine oxidation of O-silylated phenols bearing various types of aminoquinones at the para position in 2,2,2-trifluoroethanol gave azacarbocyclic spiro dienones in good yields. Using this method, the first total synthesis of discorhabdin C, which was isolated from the sponge of Latrunculia du Bocage in New Zealand, was achieved.

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U2 - 10.1021/ja00032a036

DO - 10.1021/ja00032a036

M3 - 学術論文

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JF - Journal of the American Chemical Society

IS - 6

ER -

Total Synthesis of Discorhabdin C: A General Aza Spiro Dienone Formation from O-Silylated Phenol Derivatives Using a Hypervalent Iodine Reagent

Abstract

ASJC Scopus subject areas

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