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^*

^*Corresponding author for this work

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

19 Citations (Scopus)

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
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
Publication status	Published - 2019 Jun 7

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Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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 = "Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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

language = "English",

volume = "21",

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journal = "Organic Letters",

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AU - Jo, Young In

AU - Burke, Martin D.

AU - Cheon, Cheol Hong

PY - 2019/6/7

Y1 - 2019/6/7

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.

UR - https://www.scopus.com/pages/publications/85066956976

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DO - 10.1021/acs.orglett.9b01397

M3 - Article

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SN - 1523-7060

VL - 21

SP - 4201

EP - 4204

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Modular Syntheses of Phenanthroindolizidine Natural Products

Abstract

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ASJC Scopus subject areas

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