Bioinspired Total Synthesis of 3-epi-Junipercedrol

被引：1

作者：

Xiao, Jian ^{[1
]}

Liu, Zi-Hao ^{[2
]}

He, Zi-Fan ^{[1
]}

Wu, Ping ^{[1
]}

Wang, Ya-Wen ^{[1
]}

Li, Wei-Dong Z. ^{[1
]}

Peng, Yu ^{[1
]}

机构：

[1] Southwest Jiaotong Univ, Sch Chem, Key Lab Adv Technol Mat, Minist Educ, Chengdu 610031, Peoples R China

[2] Southwest Jiaotong Univ, Sch Life Sci & Engn, Key Lab Adv Technol Mat, Minist Educ,Sch Chem, Chengdu 610031, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 35期

基金：

中国国家自然科学基金;

关键词：

TRICYCLIC SESQUITERPENES; DERIVATIVES; MIGRATIONS;

D O I：

10.1021/acs.orglett.4c02877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bioinspired total synthesis of 3-epi-junipercedrol, which contains a strained tricyclo[5.2.2.0(3,7)]undecane allo-cedrane framework and five stereocenters, was accomplished via an effective anionic semipinacol rearrangement of a tricyclic cedrane mesylate. The corresponding cedrane precursor was synthesized efficiently by employing the reductive oxy-Nazarov cyclization and an intramolecular aldol condensation as the key steps. This synthetic approach provided a further evidence for the biogenetic relationship between the typical cedrane and allo-cedrane sesquiterpenoids.

引用

页码：7463 / 7467

页数：5

共 50 条

[21] Bioinspired Total Synthesis of Bussealin E
Twigg, David G.
Baldassarre, Leonardo
Frye, Elizabeth C.
Galloway, Warren R. J. D.
Spring, David R.
ORGANIC LETTERS, 2018, 20 (06) : 1597 - 1599
[22] Bioinspired total synthesis of (-)-gymnothelignan L
Chen, Peng
Huo, Liang
Li, Huilin
Liu, Lin
Yuan, Ziyun
Zhang, Hao
Feng, Shangbiao
Xie, Xingang
Wang, Xiaolei
She, Xuegong
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (07): : 1124 - 1128
[23] Bioinspired Total Synthesis of Bipolarolides A and B
Li, Bo
Tan, Chuanzhen
Ma, Tianhao
Jia, Yanxing
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (10)
[24] Bioinspired Total Synthesis of Hyperireflexolides A and B
zur Bonsen, Andreas B.
Sumby, Christopher J.
George, Jonathan H.
ORGANIC LETTERS, 2023, 25 (34) : 6317 - 6321
[25] Total synthesis of 6-epi-sarsolilide A
Zhang, JZ
Xu, XX
TETRAHEDRON LETTERS, 2000, 41 (06) : 941 - 943
[26] Total synthesis of (±)-2-epi-validamine
Okamura, Hiroaki
Nagaike, Hiroshi
Kipassa, Nsiama Tienabe
Iwagawa, Tetsuo
Nakatani, Munehiro
HETEROCYCLES, 2006, 68 (12) : 2587 - 2594
[27] A STEREOSELECTIVE TOTAL SYNTHESIS OF EPI-LUPININE
BREMMER, ML
WEINREB, SM
TETRAHEDRON LETTERS, 1983, 24 (03) : 261 - 264
[28] The convergent total synthesis of cytotoxic homospisulosine and its 3-epi-analogue
Stankova, Kvetoslava
Martinkova, Miroslava
Gonda, Jozef
Bago, Martina
Pilatova, Martina
Goenciova, Gabriela
TETRAHEDRON-ASYMMETRY, 2015, 26 (24) : 1394 - 1407
[29] Total Synthesis of (±)-7-epi-Nemorosone
Zhang, Qiang
Porco, John A., Jr.
ORGANIC LETTERS, 2012, 14 (07) : 1796 - 1799
[30] First Total Synthesis of 3-Epi-calystegin B2
Csuk, Rene
Reissmann, Stefan
Kluge, Ralph
Stroehl, Dieter
Korb, Claudia
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2011, 66 (03): : 317 - 323

← 1 2 3 4 5 →