Total synthesis of (+)-rutamarin

Yi Nan Zhang; Shi Lei Zhang; Lei Ma; Yu Zhang; Xu Shen; Wei Wang; Li Hong Hu

doi:10.1002/adsc.200800396

Total synthesis of (+)-rutamarin

Yi Nan Zhang, Shi Lei Zhang, Lei Ma, Yu Zhang, Xu Shen, Wei Wang, Li Hong Hu

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

11 Scopus citations

Abstract

The first enantioselective total synthesis of (+)-rutamarin (1) is described. The synthetic route features the highlyenantiose lective construction of the stereogenic center via the Sharpless asymmetric dihydroxylation (99% ee), the facile assemblyof quaternarycarb on-centered 3-substituted side chain and high synthetic efficiency from readily available starting materials. Furthermore, the synthetic strategy could be readilyadopt ed for the synthesis of (+)-rutamarin analogues.

Original language	English (US)
Pages (from-to)	2373-2379
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	350
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.200800396
State	Published - Oct 6 2008
Externally published	Yes

Keywords

Asymmetric synthesis
Furanocoumarins
Rutamarin
Sharpless asymmetric dihydroxylation

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200800396

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title = "Total synthesis of (+)-rutamarin",

abstract = "The first enantioselective total synthesis of (+)-rutamarin (1) is described. The synthetic route features the highlyenantiose lective construction of the stereogenic center via the Sharpless asymmetric dihydroxylation (99% ee), the facile assemblyof quaternarycarb on-centered 3-substituted side chain and high synthetic efficiency from readily available starting materials. Furthermore, the synthetic strategy could be readilyadopt ed for the synthesis of (+)-rutamarin analogues.",

keywords = "Asymmetric synthesis, Furanocoumarins, Rutamarin, Sharpless asymmetric dihydroxylation",

author = "Zhang, {Yi Nan} and Zhang, {Shi Lei} and Lei Ma and Yu Zhang and Xu Shen and Wei Wang and Hu, {Li Hong}",

year = "2008",

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doi = "10.1002/adsc.200800396",

language = "English (US)",

volume = "350",

pages = "2373--2379",

journal = "Advanced Synthesis and Catalysis",

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TY - JOUR

T1 - Total synthesis of (+)-rutamarin

AU - Zhang, Yi Nan

AU - Zhang, Shi Lei

AU - Ma, Lei

AU - Zhang, Yu

AU - Shen, Xu

AU - Wang, Wei

AU - Hu, Li Hong

PY - 2008/10/6

Y1 - 2008/10/6

N2 - The first enantioselective total synthesis of (+)-rutamarin (1) is described. The synthetic route features the highlyenantiose lective construction of the stereogenic center via the Sharpless asymmetric dihydroxylation (99% ee), the facile assemblyof quaternarycarb on-centered 3-substituted side chain and high synthetic efficiency from readily available starting materials. Furthermore, the synthetic strategy could be readilyadopt ed for the synthesis of (+)-rutamarin analogues.

AB - The first enantioselective total synthesis of (+)-rutamarin (1) is described. The synthetic route features the highlyenantiose lective construction of the stereogenic center via the Sharpless asymmetric dihydroxylation (99% ee), the facile assemblyof quaternarycarb on-centered 3-substituted side chain and high synthetic efficiency from readily available starting materials. Furthermore, the synthetic strategy could be readilyadopt ed for the synthesis of (+)-rutamarin analogues.

KW - Asymmetric synthesis

KW - Furanocoumarins

KW - Rutamarin

KW - Sharpless asymmetric dihydroxylation

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DO - 10.1002/adsc.200800396

M3 - Article

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SN - 1615-4150

VL - 350

SP - 2373

EP - 2379

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 14-15

ER -

Total synthesis of (+)-rutamarin

Abstract

Keywords

ASJC Scopus subject areas

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