A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines

Shen H. Tan; Martin G. Banwell; Anthony C. Willis

doi:10.1021/acs.joc.6b01400

A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines

Shen H. Tan, Martin G. Banwell^*, Anthony C. Willis

^*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

Perhydroquinoline 4, the product of a Raney-cobalt mediated reductive cyclization reaction, was readily converted into the cis-ring-fused perhydroquinoline 15 that could be epimerized to its trans-fused counterpart 2 on sequential treatment with iodosylbenzene then sodium borohydride. Tetracycle 2 is an advanced intermediate associated with a recently reported total synthesis of the alkaloid kopsihainanine A (1).

Original language	English
Pages (from-to)	8022-8028
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	81
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.6b01400
Publication status	Published - 2 Sept 2016

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abstract = "Perhydroquinoline 4, the product of a Raney-cobalt mediated reductive cyclization reaction, was readily converted into the cis-ring-fused perhydroquinoline 15 that could be epimerized to its trans-fused counterpart 2 on sequential treatment with iodosylbenzene then sodium borohydride. Tetracycle 2 is an advanced intermediate associated with a recently reported total synthesis of the alkaloid kopsihainanine A (1).",

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AU - Tan, Shen H.

AU - Banwell, Martin G.

AU - Willis, Anthony C.

PY - 2016/9/2

Y1 - 2016/9/2

N2 - Perhydroquinoline 4, the product of a Raney-cobalt mediated reductive cyclization reaction, was readily converted into the cis-ring-fused perhydroquinoline 15 that could be epimerized to its trans-fused counterpart 2 on sequential treatment with iodosylbenzene then sodium borohydride. Tetracycle 2 is an advanced intermediate associated with a recently reported total synthesis of the alkaloid kopsihainanine A (1).

AB - Perhydroquinoline 4, the product of a Raney-cobalt mediated reductive cyclization reaction, was readily converted into the cis-ring-fused perhydroquinoline 15 that could be epimerized to its trans-fused counterpart 2 on sequential treatment with iodosylbenzene then sodium borohydride. Tetracycle 2 is an advanced intermediate associated with a recently reported total synthesis of the alkaloid kopsihainanine A (1).

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U2 - 10.1021/acs.joc.6b01400

DO - 10.1021/acs.joc.6b01400

M3 - Article

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SP - 8022

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines

Abstract

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