Total Synthesis of Indole Alkaloid Alsmaphorazine D

被引：34

作者：

Zhu, Chenlong ^{[1
]}

Liu, Zhaobo ^{[1
]}

Chen, Guanyu ^{[1
]}

Zhang, Kai ^{[1
]}

Ding, Hanfeng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 03期

关键词：

cyclization; epimerization; oxidative coupling; pyrroloindoles; total synthesis; ENANTIOSPECIFIC TOTAL-SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; MACROCYCLIZATION-TRANSANNULAR CYCLIZATION; CERIUM(IV) AMMONIUM-NITRATE; GENERAL-APPROACH; ALSTONIA-SCHOLARIS; STEREOCHEMICAL CONTROL; RADICAL CYCLIZATIONS; BREVIANAMIDE E; IN-VITRO;

D O I：

10.1002/anie.201409827

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise total synthesis of rac-alsmaphorazine D has been described for the first time. The efficient synthetic strategy features four key transformations: 1) a catalytic intramolecular oxidative cyclization for the delta-lactamindole backbone; 2) an oxidative cyclic aminal formation for the hexahydropyrrolo[2,3-b]pyrrole framework; 3) a transannular radical cyclization for the construction of the diazabicyclo-[3.3.1]nonane structure; and 4) a one-pot desilylation/double epimerization reaction that affirms the relative stereochemistry.

引用

页码：879 / 882

页数：4

共 65 条

[51]

2-6

[52] INTRAMOLECULAR NITROGEN ASSISTANCE IN THE NICKEL-PROMOTED TANDEM CYCLIZATION-CAPTURE OF AMINO-TETHERED VINYL BROMIDES AND ALKENES [J].

SOLE, D ;

CANCHO, Y ;

LLEBARIA, A ;

MORETO, JM ;

DELGADO, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12133-12134

[53] Total synthesis of (+)-madindoline A and (-)-madindoline B, potent, selective inhibitors of interleukin 6. Determination of the relative and absolute configurations [J].

Sunazuka, T ;

Hirose, T ;

Shirahata, T ;

Harigaya, Y ;

Hayashi, M ;

Komiyama, K ;

Omura, S ;

Smith, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (09) :2122-2123

[54] Total Synthesis of the Monoterpenoid Indole Alkaloid (±)-Aspidophylline A [J].

Teng, Mingxing ;

Zi, Weiwei ;

Ma, Dawei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) :1814-1817

[55]

Tsai AI, 2005, HETEROCYCLES, V65, P2381

[56] Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis [J].

Umehara, Atsushi ;

Ueda, Hirofumi ;

Tokuyama, Hidetoshi .

ORGANIC LETTERS, 2014, 16 (09) :2526-2529

[57] Intramolecular cyclization of 2,7- or 2,8-bis-unsaturated esters mediated by (eta(2)-propene)Ti(O-i-Pr)(2). Facile construction of mono- and bicyclic skeletons with stereoselective introduction of a side chain. A synthesis of d-sabinene [J].

Urabe, H ;

Suzuki, K ;

Sato, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (42) :10014-10027

[58] General approach for the synthesis of sarpagine/ajmaline indole alkaloids. Stereospecific total synthesis of the sarpagine alkaloid (+)-vellosimine [J].

Wang, T ;

Cook, JM .

ORGANIC LETTERS, 2000, 2 (14) :2057-2059

[59] STEREOCHEMICAL CONTROL OF TRANS-ANNULAR RADICAL CYCLIZATIONS - A NEW APPROACH TO THE SYNTHESIS OF LINEARLY FUSED CYCLOPENTANOIDS [J].

WINKLER, JD ;

SRIDAR, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (07) :1708-1709

[60] Highly enantioselective atom-transfer radical cyclization reactions catalyzed by chiral Lewis acids [J].

Yang, D ;

Gu, S ;

Yan, YL ;

Zhu, NY ;

Cheung, KK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (35) :8612-8613

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