Studies directed towards the total synthesis of (+)-sieboldine A

Progress towards the total synthesis of sieboldine A is described. This synthetic approach uses a nickel-catalyzed alkyne-ketone reductive cyclization to form the hydrindane core of the natural product in good yield and with excellent diastereoselectivity about the newly formed tertiary allylic alcohol ... The hydrindane product from this reductive cyclization can be transformed into the tetracyclic N,O-acetal which is two steps removed from the natural product 1. Efforts directed towards completion of the synthesis of 1 via a direct late-stage amine oxidation are presented ...

Department dc:contributor.department

Massachusetts Institute of Technology. Dept. of Chemistry.

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2008

Author dc:creator

• Gehling, Victor S. (Victor Scott)

Advisor dc:contributor.advisor

• Timothy F. Jamison.

• Chemistry.

Statement dc:rights

• M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/1721.1/43766

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/43766