Oxidative Cyclization Reactions of Tryptamine Utilizing Hypervalent Iodobenzene in Routes for Pyrroloindole Alkaloid Synthesis

被引：28

作者：

Kajiyama, Daichi ^{[1
]}

Saitoh, Tsuyoshi ^{[1
]}

Yamaguchi, Satoshi ^{[1
]}

Nishiyama, Shigeru ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 11期

关键词：

cyclization; fused ring systems; indole; natural products; oxidation; IODINE OXIDANT; DERIVATIVES; SKELETON;

D O I：

10.1055/s-0031-1291006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative cyclization of N-acetyltryptamine by using iodobenzene diacetate (PIDA) provided the corresponding 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-ol derivative, which could be derivatized following appropriate protection of the two amino and tert-hydroxyl groups. The facile one-pot procedure for cyclization and introduction of the oxygen functionality was applied in concise routes for the synthesis of the natural products CPC-1 and debromoflustraminol B.

引用

页码：1667 / 1671

页数：5

共 50 条

[1] Alkaloid Synthesis by Means of Hypervalent Iodobenzene
Saitoh, Tsuyoshi
Nishiyama, Shigeru
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (10) : 1120 - 1130
[2] Iodobenzene-Catalyzed Intramolecular Oxidative Cyclization Reactions of δ-Alkynyl β-Ketoesters
Rodriguez, Arantxa
Moran, Wesley J.
ORGANIC LETTERS, 2011, 13 (09) : 2220 - 2223
[3] Iodobenzene-Catalyzed Oxidative Cyclization for the Synthesis of Highly Functionalized Cyclopropanes
Li, Yang
Guo, Hao
Fan, Renhua
SYNTHESIS-STUTTGART, 2020, 52 (06): : 928 - 932
[4] Hypervalent Iodine-Mediated Synthesis of Spiroheterocycles via Oxidative Cyclization
Xing, Linlin
Zhang, Yong
Du, Yunfei
CURRENT ORGANIC CHEMISTRY, 2019, 23 (01) : 14 - 37
[5] Total synthesis of the coccinellid alkaloid (±)-adalinine utilizing a nitrenium ion cyclization
Wardrop, DJ
Landrie, CL
Ortíz, JA
SYNLETT, 2003, (09) : 1352 - 1354
[6] Synthesis of Spiroguanidine Derivatives by Dearomative Oxidative Cyclization using Hypervalent Iodine Reagent
Odagi, Minami
Okuda, Kazuma
Ishizuka, Hayate
Adachi, Kanna
Nagasawa, Kazuo
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (02) : 218 - 221
[7] Regioselective synthesis of isoxazoles by hypervalent iodine(III) reagent mediated oxidative cyclization
Jarvi, Melissa
Rohde, Greg
Nemykin, Victor
Zhdankin, Viktor
Yoshimura, Akira
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[8] Synthesis of Tetrahydropyrroloiminoquinone Alkaloids Based on Electrochemically Generated Hypervalent Iodine Oxidative Cyclization
Inoue, Keisuke
Ishikawa, Yuichi
Nishiyama, Shigeru
ORGANIC LETTERS, 2010, 12 (03) : 436 - 439
[9] Utilizing exchange reactions at hypervalent iodine centers for the synthesis of polymeric materials
Han, Hongzhang
Tsarevsky, Nicolay V.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
[10] Hypervalent Iodine(III)-Induced Domino Oxidative Cyclization for the Synthesis of Cyclopenta[b]furans
Lin, Mei-Huey
Chen, Yu-Chun
Chiu, Shih-Hao
Chen, Yun-Fan
Chuang, Tsung-Hsun
MOLECULES, 2016, 21 (12)

← 1 2 3 4 5 →