Enantioselective Total Synthesis and Absolute Configuration of Apiosporic Acid

被引:12
|
作者
Gaertner, Martin [1 ]
Kossler, David [1 ]
Pflaesterer, Daniel [1 ]
Helmchen, Guenter [1 ]
机构
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
来源
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 09期
关键词
CROSS-COUPLING REACTION; STEREOCHEMISTRY; OLEFINATION; ALDEHYDES; YLIDES;
D O I
10.1021/jo300519g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of the polyketide apiosporic acid is presented. Key steps are a Julia-Kocienski olefination, a Suzuki-Miyaura cross-coupling, and an intramolecular Diels-Alder reaction. The absolute configuration of the natural product was determined.
引用
收藏
页码:4491 / 4495
页数:5
相关论文
共 50 条
  • [21] Total Synthesis and Absolute Configuration of the Natural Amino Acid Tetrahydrolathyrine
    Benohoud, Meryem
    Leman, Loic
    Cardoso, Silvia H.
    Retailleau, Pascal
    Dauban, Philippe
    Thierry, Josiane
    Dodd, Robert H.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5331 - 5336
  • [22] ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE-CONFIGURATION OF MYOPORONE
    ANAND, RC
    SINGH, V
    TETRAHEDRON, 1993, 49 (29) : 6515 - 6520
  • [23] First enantioselective total synthesis of a naturally occurring dolabellane. Revision of absolute configuration
    Corey, EJ
    Kania, RS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (05) : 1229 - 1230
  • [24] Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Tronocarpine by an Asymmetric Michael/Aldol Reaction
    Tan, Dong-Xing
    Zhou, Jie
    Liu, Chao-You
    Han, Fu-She
    Advanced Materials, 2020, 59 (10) : 3862 - 3867
  • [25] Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids
    Lee, Jungeun
    Yuan, Yue
    Lee, Sanha
    Kwon, Sang-Il
    Seo, Seung-yong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [26] Enantioselective synthesis and absolute configuration determination of hydroxywilfordic acid in sesquiterpene pyridine alkaloids
    Yuan, Yue
    Jung, Jong-Wha
    Seo, Seung-Yong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (01) : 44 - 48
  • [27] Total synthesis and absolute configuration of (-)-anthoplalone
    Hanessian, S
    Cantin, LD
    Andreotti, D
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13): : 4893 - 4900
  • [28] Total Synthesis and Absolute Configuration of (-)-Gummiferol
    Takamura, Hiroyoshi
    Wada, Hiroko
    Lu, Nan
    Kadota, Isao
    ORGANIC LETTERS, 2011, 13 (14) : 3644 - 3647
  • [29] Total Synthesis and Absolute Configuration of Raputindole A
    Kock, Mario
    Jones, Peter G.
    Lindel, Thomas
    ORGANIC LETTERS, 2017, 19 (23) : 6296 - 6299
  • [30] Total synthesis and absolute configuration of koshikalide
    Kunifuda, Kazuki
    Iwasaki, Arihiro
    Nagamoto, Masashi
    Suenaga, Kiyotake
    TETRAHEDRON LETTERS, 2016, 57 (29) : 3121 - 3123