Modular Syntheses of Phenanthroindolizidine Natural Products

Young In Jo; Martin D. Burke; Cheol Hong Cheon

doi:10.1021/acs.orglett.9b01397

Modular Syntheses of Phenanthroindolizidine Natural Products

Young In Jo, Martin D. Burke, Cheol Hong Cheon

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

Abstract

A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.

Original language	English (US)
Pages (from-to)	4201-4204
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.9b01397
State	Published - Jun 7 2019
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b01397

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title = "Modular Syntheses of Phenanthroindolizidine Natural Products",

abstract = "A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.",

author = "Jo, {Young In} and Burke, {Martin D.} and Cheon, {Cheol Hong}",

note = "Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2018R1D1A1A02086110 and NRF-2014-011165, Center for New Directions in Organic Synthesis), and by a grant from the National Institutes of Health, U.S.A. (NIH GM118185) to M.D.B. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b01397",

language = "English (US)",

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AU - Burke, Martin D.

AU - Cheon, Cheol Hong

N1 - Funding Information: This work was supported by National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2018R1D1A1A02086110 and NRF-2014-011165, Center for New Directions in Organic Synthesis), and by a grant from the National Institutes of Health, U.S.A. (NIH GM118185) to M.D.B. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/6/7

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N2 - A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.

AB - A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.

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Modular Syntheses of Phenanthroindolizidine Natural Products

Abstract

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