Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis

Koji Ochiai; Sankar Kuppusamy; Yusuke Yasui; Kenji Harada; Nishant R. Gupta; Yohei Takahashi; Takaaki Kubota; Jun'ichi Kobayashi; Yujiro Hayashi

doi:10.1002/chem.201504675

Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis

Koji Ochiai, Sankar Kuppusamy, Yusuke Yasui, Kenji Harada, Nishant R. Gupta, Yohei Takahashi, Takaaki Kubota, Jun'ichi Kobayashi, Yujiro Hayashi

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

11 Citations (Scopus)

Abstract

The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP "linchpin" as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.

Original language	English
Pages (from-to)	3287-3291
Number of pages	5
Journal	Chemistry - A European Journal
Volume	22
Issue number	10
DOIs	https://doi.org/10.1002/chem.201504675
Publication status	Published - Mar 1 2016
Externally published	Yes

Keywords

Enders RMAP
Grieco-Nishizawa olefination
Keck allylation
Shi-epoxidation
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201504675

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Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II : Synthesis of C17-C29 Subunit and Completion of the Synthesis. / Ochiai, Koji; Kuppusamy, Sankar; Yasui, Yusuke; Harada, Kenji; Gupta, Nishant R.; Takahashi, Yohei; Kubota, Takaaki; Kobayashi, Jun'ichi; Hayashi, Yujiro.

In: Chemistry - A European Journal, Vol. 22, No. 10, 01.03.2016, p. 3287-3291.

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

Ochiai, K, Kuppusamy, S, Yasui, Y, Harada, K, Gupta, NR, Takahashi, Y, Kubota, T, Kobayashi, J & Hayashi, Y 2016, 'Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis', Chemistry - A European Journal, vol. 22, no. 10, pp. 3287-3291. https://doi.org/10.1002/chem.201504675

Ochiai, Koji ; Kuppusamy, Sankar ; Yasui, Yusuke ; Harada, Kenji ; Gupta, Nishant R. ; Takahashi, Yohei ; Kubota, Takaaki ; Kobayashi, Jun'ichi ; Hayashi, Yujiro. / Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II : Synthesis of C17-C29 Subunit and Completion of the Synthesis. In: Chemistry - A European Journal. 2016 ; Vol. 22, No. 10. pp. 3287-3291.

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abstract = "The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP {"}linchpin{"} as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.",

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AU - Kuppusamy, Sankar

AU - Yasui, Yusuke

AU - Harada, Kenji

AU - Gupta, Nishant R.

AU - Takahashi, Yohei

AU - Kubota, Takaaki

AU - Kobayashi, Jun'ichi

AU - Hayashi, Yujiro

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AB - The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP "linchpin" as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.

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Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis

Abstract

Keywords

ASJC Scopus subject areas

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