Total synthesis of (+)-suaveolindole: Establishment of its absolute configuration Journal Article
| Authors: | Velthuisen, E. J.; Danishefsky, S. J. |
| Article Title: | Total synthesis of (+)-suaveolindole: Establishment of its absolute configuration |
| Abstract: | This communication describes two approaches toward the total synthesis of (+)-suaveolindole. The initial strategy uses a 6-exo-Heck cyclization to generate a transient sp3 carbopalladate. This intermediate was successfully coupled with an indole 3-stannane to assemble the majority of the carbon framework of the natural product. However, due to problems described herein, this interesting route was not viable. To reach our target, lessons learned from the first strategy directed us to develop a significant extension of the Ireland ester enolate rearrangement in which the tetra-substituted isopropylidene group and the α-disposed carboxymethyl function are introduced in a single event. This key reaction enables a remarkably concise inaugural synthesis of (+)-suaveolindole. Copyright © 2007 American Chemical Society. |
| Keywords: | unclassified drug; chemical analysis; drug structure; drug synthesis; antiinfective agent; chemistry; anti-bacterial agents; conformation; cyclization; structure analysis; molecular conformation; chemical reaction; synthesis; sesquiterpenes; sesquiterpene; isoprenoid; suaveolindole |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 129 |
| Issue: | 35 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2007-09-05 |
| Start Page: | 10640 |
| End Page: | 10641 |
| Language: | English |
| DOI: | 10.1021/ja075100k |
| PUBMED: | 17696355 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 9" - "Export Date: 17 November 2011" - "CODEN: JACSA" - "Source: Scopus" |
