Total synthesis of (±)-Aplykurodinone-1: Traceless stereochemical guidance Journal Article
| Authors: | Zhang, Y.; Danishefsky, S. J. |
| Article Title: | Total synthesis of (±)-Aplykurodinone-1: Traceless stereochemical guidance |
| Abstract: | The total synthesis of the highly degraded steroidal natural product, aplykurodinone-1 (1), has been accomplished. Key features include a one-flask hydrolysis/retro-aldol/iodolactonization sequence to excise the C8 hydroxymethylene functionality with retention of stereochemistry and the stereoselective installation of the C13 methyl group through hydrogenation with homogeneous catalyst. © 2010 American Chemical Society. |
| Keywords: | unclassified drug; steroid; drug synthesis; chemistry; natural product; hydrolysis; catalyst; chemical reaction; synthesis; key feature; total synthesis; stereochemistry; indan derivative; stereoisomerism; cycloaddition; stereo-selective; lactones; hydrogenation; natural products; methyl group; homogeneous catalyst; hydrocarbons; aplykurodinone; carbon 13; aplykurodinone 1; aplykurodinone-1; lactone; aldol reaction; iodolactonization; indans |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 132 |
| Issue: | 28 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2010-07-21 |
| Start Page: | 9567 |
| End Page: | 9569 |
| Language: | English |
| DOI: | 10.1021/ja1035495 |
| PUBMED: | 20513158 |
| PROVIDER: | scopus |
| PMCID: | PMC2912429 |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 3" - "Export Date: 20 April 2011" - "CODEN: JACSA" - "Source: Scopus" |
