Asymmetric Total Synthesis of Phomarol

Fan，Jian Hong1,2; Wang，Jing Jing1; Li，Fangfang1; Wang，Guannan1; Guo，Qiang1; Chung，Lung Wa1; Li，Chuang Chuang1

2021-12-01

10.31635/ccschem.021.202000721

CCS Chemistry   影响因子和分区

2096-5745

2096-5745

The first and asymmetric total synthesis of phomarol, an uncommon C25 steroid, is described. The synthetically challenging benzocycloheptane motif, found in phomarol and some other naturally occurring molecules, was synthesized efficiently using a very mild acid-promoted type I [5 + 2] cycloaddition, followed by regio- and chemoselective cleavage of the C–O bond and aromatization cascade. This work is the first example of using the hydrogen bonding between the hydroxy group and oxidopyrylium ylide to control the stereoselectivity of cycloadditions. The highly functionalized tetrahydropyran ring of phomarol was produced efficiently based on our suggested biomimetic pathway.

Aromatization cascade Phomarol Steroid Total synthesis [5 + 2] cycloaddition

ESCI

英语

第一

Natural Science Foundation of China[21672095,21971105] ; Shenzhen Science and Technology Innovation Committee["ZDSYS20190902093215877","KQTD2016053117035204"]

Chemistry

Chemistry, Multidisciplinary

WOS:000794252300021

CHINESE CHEMICAL SOC

2-s2.0-85112528282

Scopus

1.Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis,Department of Chemistry,Shenzhen Grubbs Institute,Southern University of Science and Technology,Shenzhen,518055,China
2.Institute of Chinese Medical Sciences,University of Macau,999078,Macao

Fan，Jian Hong,Wang，Jing Jing,Li，Fangfang,et al. Asymmetric Total Synthesis of Phomarol[J]. CCS Chemistry,2021,3(12):348-357.

Fan，Jian Hong.,Wang，Jing Jing.,Li，Fangfang.,Wang，Guannan.,Guo，Qiang.,...&Li，Chuang Chuang.(2021).Asymmetric Total Synthesis of Phomarol.CCS Chemistry,3(12),348-357.

Fan，Jian Hong,et al."Asymmetric Total Synthesis of Phomarol".CCS Chemistry 3.12(2021):348-357.