Total Synthesis of Scabrolide F

Hiroyoshi Takamura; Yuki Sugitani; Ryohei Morishita; Isao Kadota

doi:10.1021/acs.orglett.2c03263

Total Synthesis of Scabrolide F

Hiroyoshi Takamura, Yuki Sugitani, Ryohei Morishita, Isao Kadota

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

Abstract

The first total synthesis of scabrolide F, a norcembranolide isolated from the soft coral Sinularia scabra, is described. Hydroxycarboxylic acid, which is the key synthetic intermediate, was synthesized in a convergent manner by fragment coupling. The obtained hydroxycarboxylic acid was subjected to macrolactonization and subsequent transannular ring-closing metathesis (RCM) to furnish scabrolide F. The synthetic protocol can be extended to the total synthesis of other norcembranolides.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.2c03263
Publication status	Accepted/In press - 2022

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.2c03263

Cite this

@article{f030d8b0509f497ba7464eeaeeea8b40,

title = "Total Synthesis of Scabrolide F",

abstract = "The first total synthesis of scabrolide F, a norcembranolide isolated from the soft coral Sinularia scabra, is described. Hydroxycarboxylic acid, which is the key synthetic intermediate, was synthesized in a convergent manner by fragment coupling. The obtained hydroxycarboxylic acid was subjected to macrolactonization and subsequent transannular ring-closing metathesis (RCM) to furnish scabrolide F. The synthetic protocol can be extended to the total synthesis of other norcembranolides.",

author = "Hiroyoshi Takamura and Yuki Sugitani and Ryohei Morishita and Isao Kadota",

note = "Funding Information: We are grateful to Prof. Jyh-Horng Sheu (National Sun Yat-sen University) and Prof. Atallah F. Ahmed (King Saud University) for the valuable discussion on natural scabrolide F. We thank the Division of Instrumental Analysis, Okayama University, for assistance with the NMR and HRMS measurements. This work was supported by JSPS KAKENHI Grant Number JP21H01938. Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

doi = "10.1021/acs.orglett.2c03263",

language = "English",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Total Synthesis of Scabrolide F

AU - Takamura, Hiroyoshi

AU - Sugitani, Yuki

AU - Morishita, Ryohei

AU - Kadota, Isao

N1 - Funding Information: We are grateful to Prof. Jyh-Horng Sheu (National Sun Yat-sen University) and Prof. Atallah F. Ahmed (King Saud University) for the valuable discussion on natural scabrolide F. We thank the Division of Instrumental Analysis, Okayama University, for assistance with the NMR and HRMS measurements. This work was supported by JSPS KAKENHI Grant Number JP21H01938. Publisher Copyright: © 2022 American Chemical Society.

PY - 2022

Y1 - 2022

N2 - The first total synthesis of scabrolide F, a norcembranolide isolated from the soft coral Sinularia scabra, is described. Hydroxycarboxylic acid, which is the key synthetic intermediate, was synthesized in a convergent manner by fragment coupling. The obtained hydroxycarboxylic acid was subjected to macrolactonization and subsequent transannular ring-closing metathesis (RCM) to furnish scabrolide F. The synthetic protocol can be extended to the total synthesis of other norcembranolides.

AB - The first total synthesis of scabrolide F, a norcembranolide isolated from the soft coral Sinularia scabra, is described. Hydroxycarboxylic acid, which is the key synthetic intermediate, was synthesized in a convergent manner by fragment coupling. The obtained hydroxycarboxylic acid was subjected to macrolactonization and subsequent transannular ring-closing metathesis (RCM) to furnish scabrolide F. The synthetic protocol can be extended to the total synthesis of other norcembranolides.

UR - http://www.scopus.com/inward/record.url?scp=85140843647&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85140843647&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.2c03263

DO - 10.1021/acs.orglett.2c03263

M3 - Article

C2 - 36264039

AN - SCOPUS:85140843647

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Total Synthesis of Scabrolide F

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this