Asymmetric Formal Synthesis of (+)-Pyrenolide D

被引：9

作者：

Markovic, Martin ^{[1
]}

Lopatka, Pavol ^{[1
]}

Koos, Peter ^{[2
]}

Gracza, Tibor ^{[1
]}

机构：

[1] Slovak Univ Technol Bratislava, Dept Organ Chem, Bratislava 81237, Slovakia

[2] Georganics Ltd, Bratislava 81103, Slovakia

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 06期

关键词：

natural products; pyrenolide D; oxycarbonylation; palladium catalysis; iron pentacarbonyl; PALLADIUM(II)-CATALYZED OXYCARBONYLATION; UNSATURATED POLYOLS;

D O I：

10.1055/s-0033-1338584

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, asymmetric formal synthesis of (+)-pyrenolide D from (E)-crotonaldehyde is described. The key steps include an enantioselective Sharpless dihydroxylation of protected hex-4-en-1-yn-3-ol and a highly diastereoselective palladium-catalysed oxycarbonylation of (2R,3S,4S)-hex-5-ene-2,3,4-triol using iron pentacarbonyl as the carbon monoxide source.

引用

页码：817 / 821

页数：5

共 50 条

[21] ASYMMETRIC FORMAL TOTAL SYNTHESIS OF (-)-SWAINSONINE
ZHOU, WS
XIE, WG
LU, ZH
PAN, XF
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (20): : 2599 - 2604
[22] Asymmetric formal synthesis of schulzeines A and C
Jang, Jaebong
Ahn, Jaeseung
Jung, Jong-Wha
Sim, Jaehoon
Chang, Dong-Jo
An, Hongchan
Kim, Dae-Duk
Suh, Young-Ger
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[23] Catalytic asymmetric formal synthesis of beraprost
Kobayashi, Yusuke
Kuramoto, Ryuta
Takemoto, Yoshiji
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 2654 - 2660
[24] The first formal asymmetric synthesis of phorbol
Wender, PA
Rice, KD
Schnute, ME
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (33) : 7897 - 7898
[25] ASYMMETRIC-SYNTHESIS OF (+)-PILOSININE - A FORMAL SYNTHESIS OF (+)-PILOCARPINE
SHAPIRO, G
CAI, CZ
TETRAHEDRON LETTERS, 1992, 33 (18) : 2447 - 2450
[26] ASYMMETRIC-SYNTHESIS OF BENZOQUINOLIZIDINES - A FORMAL SYNTHESIS OF (-)-EMETINE
GUILES, JW
MEYERS, AI
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24): : 6873 - 6878
[27] Asymmetric total synthesis of norzoanthamine and formal synthesis of zoanthenol
Chen, Yanyu
Xin, Zhengyuan
Wang, Hui
He, Haibing
Gao, Shuanhu
ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (03): : 651 - 660
[28] Asymmetric total synthesis of norzoanthamine and formal synthesis of zoanthenol
Chen, Yanyu
Xin, Zhengyuan
Wang, Hui
He, Haibing
Gao, Shuanhu
Organic Chemistry Frontiers, 2022, 10 (03): : 651 - 660
[29] Asymmetric total synthesis and formal total synthesis of (+)-Eremantholide A
Hale, Karl J.
Li, Yi
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
[30] Asymmetric total synthesis of (+)-isocryptotanshinone and formal synthesis of (-)-cryptotanshinone
Shi, Xiang
Liu, Xiaoyu
Yang, Feilong
Wang, Yong
Wang, Zhenwei
Jiao, Xiaozhen
Xie, Ping
TETRAHEDRON, 2019, 75 (30) : 3962 - 3967

← 1 2 3 4 5 →