Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B

Naoki Toyooka; Dejun Zhou; Hideo Nemoto; Yasuhiro Tezuka; Shigetoshi Kadota; Nirina R. Andriamaharavo; H. Martin Garraffo; Thomas F. Spande; John W. Daly

doi:10.1021/jo901100m

Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B

Naoki Toyooka^*, Dejun Zhou, Hideo Nemoto, Yasuhiro Tezuka, Shigetoshi Kadota, Nirina R. Andriamaharavo, H. Martin Garraffo, Thomas F. Spande, John W. Daly

^*Corresponding author for this work

Life Sciences and Bioengineering

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

19 Scopus citations

Abstract

(Chemical Equation Presented) An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R=n-C₇H₁₅, R′=n-Pr) and 14 by the present enantioselective synthesis.

Original language	English
Pages (from-to)	6784-6791
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	74
Issue number	17
DOIs	https://doi.org/10.1021/jo901100m
State	Published - 2009/09/04

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Organic Chemistry

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title = "Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B",

abstract = "(Chemical Equation Presented) An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R=n-C7H15, R′=n-Pr) and 14 by the present enantioselective synthesis.",

author = "Naoki Toyooka and Dejun Zhou and Hideo Nemoto and Yasuhiro Tezuka and Shigetoshi Kadota and Andriamaharavo, {Nirina R.} and Garraffo, {H. Martin} and Spande, {Thomas F.} and Daly, {John W.}",

year = "2009",

month = sep,

day = "4",

doi = "10.1021/jo901100m",

language = "英語",

volume = "74",

pages = "6784--6791",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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TY - JOUR

T1 - Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B

AU - Toyooka, Naoki

AU - Zhou, Dejun

AU - Nemoto, Hideo

AU - Tezuka, Yasuhiro

AU - Kadota, Shigetoshi

AU - Andriamaharavo, Nirina R.

AU - Garraffo, H. Martin

AU - Spande, Thomas F.

AU - Daly, John W.

PY - 2009/9/4

Y1 - 2009/9/4

N2 - (Chemical Equation Presented) An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R=n-C7H15, R′=n-Pr) and 14 by the present enantioselective synthesis.

AB - (Chemical Equation Presented) An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R=n-C7H15, R′=n-Pr) and 14 by the present enantioselective synthesis.

UR - http://www.scopus.com/inward/record.url?scp=69549106214&partnerID=8YFLogxK

U2 - 10.1021/jo901100m

DO - 10.1021/jo901100m

M3 - 学術論文

C2 - 19637860

AN - SCOPUS:69549106214

SN - 0022-3263

VL - 74

SP - 6784

EP - 6791

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B

Abstract

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