Asymmetric Total Synthesis of Propindilactone G, Part 1: Initial Attempts towards the Synthesis of Schiartanes

被引：12

作者：

Xu, Ling-Ming ^{[1
,2
]}

You, Lin ^{[1
,2
]}

Shan, Zhen-Hua ^{[1
,2
]}

Yu, Ruo-Cheng ^{[1
,2
]}

Zhang, Bo ^{[1
,2
]}

Li, Yuan-He ^{[1
,2
]}

Shi, Ying ^{[1
,2
]}

Chen, Jia-Hua ^{[1
,2
]}

Yang, Zhen ^{[1
,2
,3
,4
]}

机构：

[1] Peking Univ, Minist Educ, State Key Lab Bioorgan Chem & Mol Engn, Beijing Natl Lab Mol Sci BNLMS,Peking Tsinghua Ct, 202 Chengfu Rd, Beijing 100871, Peoples R China

[2] Peking Univ, Dept Chem, 202 Chengfu Rd, Beijing 100871, Peoples R China

[3] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

[4] Ocean Univ China, Sch Med & Pharm, Chinese Minist Educ, Key Lab Marine Drugs, 5 Yushan Rd, Qingdao, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2016年 / 11卷 / 09期

基金：

美国国家科学基金会;

关键词：

natural products; nortriterpenoids; propindilactone G; synthetic methods; total synthesis; PAUSON-KHAND REACTION; DIASTEREOSELECTIVE TOTAL-SYNTHESIS; NORTRITERPENOID NATURAL-PRODUCTS; CDEF RING-SYSTEM; LANCIFODILACTONE-G; STEREOCONTROLLED SYNTHESIS; SCHISANDRACEAE FAMILY; MICRANDILACTONE-A; ABC RING; FGH RING;

D O I：

10.1002/asia.201600129

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Our first-generation synthetic study towards the total synthesis of propindilactone G (1) and its analogues is reported. The key synthetic steps were an intramolecular Pauson-Khand reaction (PKR) and a vinylogous Mukaiyama reaction (VMAR). The stereoselective synthesis of the CDE ring moiety with an all-carbon quaternary center through a PKR was difficult, whilst a VMAR afforded a product with the opposite stereochemistry at the C20 position on the side chain. These results led us to redesign our synthetic strategy for the total synthesis of compound 1.

引用

页码：1406 / 1413

页数：8

共 50 条

[41] Asymmetric Total Synthesis of (-)-Spirochensilide A, Part 2: The Final Phase and Completion
Liang, Xin-Ting
Sun, Bao-Chuan
Zhang, Nan
Zhang, Zhong-Chao
Li, Yuan-He
Xu, Qian-Qian
Liu, Chang
Chen, Jia-Hua
Yang, Zhen
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (03): : 2158 - 2172
[42] Studies towards the asymmetric synthesis of inthomycin C and its incorporation into the total synthesis of oxazolomycin B
Garcia, Sandra Balcells
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
[43] TOWARDS THE TOTAL SYNTHESIS OF CLERODIN .1.
BOUCHARD, H
RENARD, PY
LALLEMAND, JY
TETRAHEDRON LETTERS, 1991, 32 (42) : 5953 - 5956
[44] PROGRESS TOWARDS A TOTAL SYNTHESIS OF TAXOL (1)
SORENSEN, EJ
CLAIBORNE, CF
GUY, RK
NANTERMET, PG
UENO, H
YANG, Z
NICOLAOU, KC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 342 - ORGN
[45] Asymmetric total synthesis of syringolide 1, a nonproteinaceous elicitor
Ishihara, J
Sugimoto, T
Murai, A
TETRAHEDRON, 1997, 53 (47) : 16029 - 16040
[46] ASYMMETRIC-SYNTHESIS AND ITS APPLICATIONS - TOWARDS THE SYNTHESIS OF BRYOSTATIN-1
MASAMUNE, S
PURE AND APPLIED CHEMISTRY, 1988, 60 (11) : 1587 - 1596
[47] ASYMMETRIC-SYNTHESIS AND ITS APPLICATIONS - TOWARDS THE SYNTHESIS OF BRYOSTATIN-1
MASAMUNE, S
CHIMIA, 1988, 42 (06) : 210 - 211
[48] Asymmetric total synthesis of Tofacitinib
Marican, Adolfo
Simirgiotis, Mario J.
Santos, Leonardo S.
TETRAHEDRON LETTERS, 2013, 54 (37) : 5096 - 5098
[49] Asymmetric total synthesis of fredericamycin A
Kita, Y
Higuchi, K
Yoshida, Y
Iio, K
Kitagaki, S
Akai, S
Fujioka, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (05) : 683 - 686
[50] Asymmetric Total Synthesis of (+)-Coprophilin
Shiina, Isamu
Umezaki, Yuma
Murata, Takatsugu
Suzuki, Kyohei
Tonoi, Takayuki
SYNTHESIS-STUTTGART, 2018, 50 (06): : 1301 - 1306

← 1 2 3 4 5 →