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

14 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

Access to Document

10.1002/chem.201504675

Cite this

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

@article{2a567ef5300644f4acdbd437b2a6e6ba,

title = "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 = "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.",

keywords = "Enders RMAP, Grieco-Nishizawa olefination, Keck allylation, Shi-epoxidation, total synthesis",

author = "Koji Ochiai and Sankar Kuppusamy and Yusuke Yasui and Kenji Harada and Gupta, {Nishant R.} and Yohei Takahashi and Takaaki Kubota and Jun'ichi Kobayashi and Yujiro Hayashi",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

month = mar,

day = "1",

doi = "10.1002/chem.201504675",

language = "English",

volume = "22",

pages = "3287--3291",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "10",

}

TY - JOUR

T1 - Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II

T2 - Synthesis of C17-C29 Subunit and Completion of the Synthesis

AU - Ochiai, Koji

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

PY - 2016/3/1

Y1 - 2016/3/1

N2 - 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.

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.

KW - Enders RMAP

KW - Grieco-Nishizawa olefination

KW - Keck allylation

KW - Shi-epoxidation

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=84959234907&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84959234907&partnerID=8YFLogxK

U2 - 10.1002/chem.201504675

DO - 10.1002/chem.201504675

M3 - Article

AN - SCOPUS:84959234907

VL - 22

SP - 3287

EP - 3291

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 10

ER -

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

Access to Document

Other files and links

Fingerprint

Cite this