HOMEPRODUCTSCOMPANYCONTACTFAQResearchDictionaryPharmaSign Up FREE or Login

Synthetic studies on aculeximycin: synthesis of C24-C40 segment by Kobayashi aldolization and epoxide rearrangements.

Abstract
Stereoselective synthesis of the C24-C40 segment of aculeximycin has been achieved by using the Kobayashi aldol reactions and epoxy-opening rearrangement reactions. The C33-C40 segment was synthesized by the Kobayashi aldol reaction followed by epoxidation and Jung rearrangement of epoxide 9, while the C25-C32 segment was constructed by the Kobayashi aldol reaction followed by epoxidation and the epoxy-opening rearrangement reaction of epoxide 13. These segments were connected by the aldol reaction and the sequential dehydration, reduction, and conversion of ethyl ester to ethyl ketone to give the C24-C40 segment 1. All stereogenic centers were constructed by substrate-controlled stereoselective reactions.
AuthorsTakuya Kato, Tomohiko Sato, Yuki Kashiwagi, Seijiro Hosokawa
JournalOrganic letters (Org Lett) Vol. 17 Issue 9 Pg. 2274-7 (May 01 2015) ISSN: 1523-7052 [Electronic] United States
PMID25905567 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Epoxy Compounds
  • Ketones
  • Macrolides
  • aculeximycin
Topics
  • Epoxy Compounds (chemical synthesis, chemistry)
  • Ketones (chemistry)
  • Macrolides (chemical synthesis, chemistry)
  • Molecular Structure
  • Stereoisomerism

Join CureHunter, for free Research Interface BASIC access!

Take advantage of free CureHunter research engine access to explore the best drug and treatment options for any disease. Find out why thousands of doctors, pharma researchers and patient activists around the world use CureHunter every day.
Realize the full power of the drug-disease research graph!


Choose Username:
Email:
Password:
Verify Password:
Enter Code Shown: