Synthesis of Javanicunines A and B, 9-Deoxy-PF1233s A and B, and Absolute Configuration Establishment of Javanicunine B

Ming Zhong Wang; Tong Xu Si; Chuen Fai Ku; Hongjie Zhang; Zheng Ming Li; Albert S C Chan

doi:10.1021/acs.joc.8b02650

Synthesis of Javanicunines A and B, 9-Deoxy-PF1233s A and B, and Absolute Configuration Establishment of Javanicunine B

Ming Zhong Wang^*
, Tong Xu Si
, Chuen Fai Ku
, Hongjie Zhang^*
, Zheng Ming Li
, Albert S C Chan

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

11 Citations (Scopus)

Abstract

Javanicunines A-B and 9-deoxy-PF1233s A-B belong to a family of natural diketomorpholines with a unique isopropenyl group at C-10b or C-5a and a hydroxyl group at C-11a or C-10b. We herein reported the first total synthesis of javanicunines A-B and 9-deoxy-PF1233s A-B. Pivotal features of the synthesis included a nucleophilic substitution reaction, followed by a Davis' oxaziridine oxidation to assemble javanicunines A-B, and a chemoselective and stereoselective oxidation with Murray's reagent to install the requisite C-10b hydroxyl group in 9-deoxy-PF1233s A-B. The present synthesis also established the absolute configuration of javanicunine B.

Original language	English
Pages (from-to)	831-839
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	84
Issue number	2
Early online date	18 Dec 2018
DOIs	https://doi.org/10.1021/acs.joc.8b02650
Publication status	Published - 18 Jan 2019

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title = "Synthesis of Javanicunines A and B, 9-Deoxy-PF1233s A and B, and Absolute Configuration Establishment of Javanicunine B",

abstract = "Javanicunines A-B and 9-deoxy-PF1233s A-B belong to a family of natural diketomorpholines with a unique isopropenyl group at C-10b or C-5a and a hydroxyl group at C-11a or C-10b. We herein reported the first total synthesis of javanicunines A-B and 9-deoxy-PF1233s A-B. Pivotal features of the synthesis included a nucleophilic substitution reaction, followed by a Davis' oxaziridine oxidation to assemble javanicunines A-B, and a chemoselective and stereoselective oxidation with Murray's reagent to install the requisite C-10b hydroxyl group in 9-deoxy-PF1233s A-B. The present synthesis also established the absolute configuration of javanicunine B.",

author = "Wang, \{Ming Zhong\} and Si, \{Tong Xu\} and Ku, \{Chuen Fai\} and Hongjie Zhang and Li, \{Zheng Ming\} and Chan, \{Albert S C\}",

note = "Funding Information: This work was financially supported by the Research Foundation for Advanced Talents (36000-18821101), China; Guangdong Natural Science Foundation (2017A030313751), China; the Science and Technology Planning Project of Guangzhou City (201707010189), China; and the Interdisciplinary Research Matching Scheme (RC-IRMS/15-16/02) of Hong Kong Baptist University, Hong Kong SAR, China.",

year = "2019",

month = jan,

day = "18",

doi = "10.1021/acs.joc.8b02650",

language = "English",

volume = "84",

pages = "831--839",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - Synthesis of Javanicunines A and B, 9-Deoxy-PF1233s A and B, and Absolute Configuration Establishment of Javanicunine B

AU - Wang, Ming Zhong

AU - Si, Tong Xu

AU - Ku, Chuen Fai

AU - Zhang, Hongjie

AU - Li, Zheng Ming

AU - Chan, Albert S C

N1 - Funding Information: This work was financially supported by the Research Foundation for Advanced Talents (36000-18821101), China; Guangdong Natural Science Foundation (2017A030313751), China; the Science and Technology Planning Project of Guangzhou City (201707010189), China; and the Interdisciplinary Research Matching Scheme (RC-IRMS/15-16/02) of Hong Kong Baptist University, Hong Kong SAR, China.

PY - 2019/1/18

Y1 - 2019/1/18

N2 - Javanicunines A-B and 9-deoxy-PF1233s A-B belong to a family of natural diketomorpholines with a unique isopropenyl group at C-10b or C-5a and a hydroxyl group at C-11a or C-10b. We herein reported the first total synthesis of javanicunines A-B and 9-deoxy-PF1233s A-B. Pivotal features of the synthesis included a nucleophilic substitution reaction, followed by a Davis' oxaziridine oxidation to assemble javanicunines A-B, and a chemoselective and stereoselective oxidation with Murray's reagent to install the requisite C-10b hydroxyl group in 9-deoxy-PF1233s A-B. The present synthesis also established the absolute configuration of javanicunine B.

AB - Javanicunines A-B and 9-deoxy-PF1233s A-B belong to a family of natural diketomorpholines with a unique isopropenyl group at C-10b or C-5a and a hydroxyl group at C-11a or C-10b. We herein reported the first total synthesis of javanicunines A-B and 9-deoxy-PF1233s A-B. Pivotal features of the synthesis included a nucleophilic substitution reaction, followed by a Davis' oxaziridine oxidation to assemble javanicunines A-B, and a chemoselective and stereoselective oxidation with Murray's reagent to install the requisite C-10b hydroxyl group in 9-deoxy-PF1233s A-B. The present synthesis also established the absolute configuration of javanicunine B.

UR - https://www.scopus.com/pages/publications/85060144624

U2 - 10.1021/acs.joc.8b02650

DO - 10.1021/acs.joc.8b02650

M3 - Journal article

C2 - 30562032

AN - SCOPUS:85060144624

SN - 0022-3263

VL - 84

SP - 831

EP - 839

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

Synthesis of Javanicunines A and B, 9-Deoxy-PF1233s A and B, and Absolute Configuration Establishment of Javanicunine B

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