Convergent synthesis of the cdef ring fragment of yessotoxin via α-cyano ethers

Tohru Oishi; Miho Suzuki; Koji Watanabe; Michio Murata

doi:10.3987/COM-06-S(O)23

Convergent synthesis of the cdef ring fragment of yessotoxin via α-cyano ethers

Tohru Oishi, Miho Suzuki, Koji Watanabe, Michio Murata

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

21 Citations (Scopus)

Abstract

The synthesis of the CDEF ring fragment of yessotoxin, a marine ladder polyether, has been achieved. Union of three components, the C ring aldehyde, the F ring diol, and trimethylsilyl cyanide, was accomplished by treatment with Sc(OTf)₃ to afford the α-cyano ether both in stepwise and one-pot reactions. The DE ring system was constructed through a ring closing metathesis reaction and reductive etherification sequence.

Original language	English
Pages (from-to)	91-98
Number of pages	8
Journal	Heterocycles
Volume	69
Issue number	1
DOIs	https://doi.org/10.3987/COM-06-S(O)23
Publication status	Published - Dec 1 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3987/COM-06-S(O)23

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abstract = "The synthesis of the CDEF ring fragment of yessotoxin, a marine ladder polyether, has been achieved. Union of three components, the C ring aldehyde, the F ring diol, and trimethylsilyl cyanide, was accomplished by treatment with Sc(OTf)3 to afford the α-cyano ether both in stepwise and one-pot reactions. The DE ring system was constructed through a ring closing metathesis reaction and reductive etherification sequence.",

author = "Tohru Oishi and Miho Suzuki and Koji Watanabe and Michio Murata",

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AU - Oishi, Tohru

AU - Suzuki, Miho

AU - Watanabe, Koji

AU - Murata, Michio

PY - 2006/12/1

Y1 - 2006/12/1

N2 - The synthesis of the CDEF ring fragment of yessotoxin, a marine ladder polyether, has been achieved. Union of three components, the C ring aldehyde, the F ring diol, and trimethylsilyl cyanide, was accomplished by treatment with Sc(OTf)3 to afford the α-cyano ether both in stepwise and one-pot reactions. The DE ring system was constructed through a ring closing metathesis reaction and reductive etherification sequence.

AB - The synthesis of the CDEF ring fragment of yessotoxin, a marine ladder polyether, has been achieved. Union of three components, the C ring aldehyde, the F ring diol, and trimethylsilyl cyanide, was accomplished by treatment with Sc(OTf)3 to afford the α-cyano ether both in stepwise and one-pot reactions. The DE ring system was constructed through a ring closing metathesis reaction and reductive etherification sequence.

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ER -

Convergent synthesis of the cdef ring fragment of yessotoxin via α-cyano ethers

Abstract

All Science Journal Classification (ASJC) codes

UN SDGs

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