Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy

被引：27

作者：

Zou, Yike

Li, Xiangqin

Yang, Yun

Berritt, Simon

Melvin, Jason

Gonzales, Stephen

Spafford, Matthew

Smith, Amos B., III ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Res Struct Matter Lab, Philadelphia, PA 19104 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 30期

基金：

美国国家卫生研究院;

关键词：

PALLADIUM-CATALYZED CONVERSION; MIYAURA COUPLING REACTIONS; NODULISPORIC ACID; ASYMMETRIC-SYNTHESIS; CARBONYL ADDITION; ALLYL HALIDES; CONSTRUCTION; ALKYLATION; REAGENTS; ARYL;

D O I：

10.1021/jacs.8b04053

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A unified synthetic strategy leading to the total synthesis of (-)-nodulisporic acids D, C, and B is described. Key synthetic transformations include a nickel-chromium-mediated cyclization, an aromatic ring functionalization employing a novel copper-promoted alkylation, a palladium-catalyzed cross-coupling cascade/indole ring construction, and a palladium-mediated regio- and diastereoselective allylic substitution/cyclization reaction, the latter to construct ring D.

引用

页码：9502 / 9511

页数：10

共 50 条

[1] Indole diterpene synthetic studies.: Total synthesis of (+)-nodulisporic acid F and construction of the heptacyclic cores of (+)-nodulisporic acids A and B and (-)-nodulisporic acid D
Smith, Amos B., III
Davulcu, Akin H.
Cho, Young Shin
Ohmoto, Kazuyuki
Kurti, Laszlo
Ishiyama, Haruaki
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13): : 4596 - 4610
[2] Studies toward the total synthesis of nodulisporic acids A, D, and E
Spafford, Matthew J.
Melvin, Jason E.
Jeon, Junha
Gonzales, Stephen S.
Smith, Amos B.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[3] Total Synthesis of (-)-Nodulisporic Acid D
Zou, Yike
Melvin, Jason E.
Gonzales, Stephen S.
Spafford, Matthew J.
Smith, Amos B., III
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (22) : 7095 - 7098
[4] Indole diterpene synthetic studies:: Development of a second-generation synthetic strategy for (+)-nodulisporic acids A and B
Smith, Amos B., III
Kurti, Laszlo
Davulcu, Akin H.
Cho, Young Shin
Ohmoto, Kazuyuki
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13): : 4611 - 4620
[5] Evolution of a synthetic strategy:: Total synthesis of (±)-Welwitindolinone A isonitrile
Reisman, Sarah E.
Ready, Joseph M.
Weiss, Matthew M.
Hasuoka, Atsushi
Hirata, Makoto
Tamaki, Kazuhiko
Ovaska, Timo V.
Smith, Catherine J.
Wood, John L.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (06) : 2087 - 2100
[6] A UNIFIED SYNTHETIC STRATEGY FOR CASBENE AND THE LATHYRANE DITERPENES TOTAL SYNTHESIS OF (-)-BERTYADIONOL
SMITH, AB
DORSEY, BD
MALAMAS, MS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 27 - ORN
[7] Unified Total Syntheses of (±)-Sessilifoliamides B, C, and D
Olivier, Wesley J.
Bissember, Alex C.
Smith, Jason A.
ORGANIC LETTERS, 2021, 23 (09) : 3437 - 3441
[8] Indole diterpenoid synthetic studies.: The total synthesis of (+)-nodulisporic acid F
Smith, AB
Davulcu, AH
Kürti, L
ORGANIC LETTERS, 2006, 8 (08) : 1665 - 1668
[9] Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B
Chapman, Lauren M.
Beck, Jordan C.
Lacker, Caitlin R.
Wu, Linglin
Reisman, Sarah E.
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (11): : 6066 - 6085
[10] Nodulisporic acids C, C1, and C2:: A series of D-ring-opened nodulisporic acids from the fungus Nodulisporium sp.
Ondeyka, JG
Byrne, K
Vesey, D
Zink, DL
Shoop, WL
Goetz, MA
Singh, SB
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (01): : 121 - 124

← 1 2 3 4 5 →