Enantioselective synthesis of the [6,6] spiroketal core of reveromycin A.
[structure: see text] Reveromycin A (1) belongs to a family of microbial polyketides with unusual structural features and biological activities. The structure of 1 is composed of a [6,6] spiroketal core decorated with highly unsaturated side chains. As a prelude to the synthesis of 1, we present herein a short, efficient, and enantioselective synthesis of the C9-C21 fragment 5 (spiroketal core) of reveromycin A.
Drouet
K E
KE
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla 92093-0358, USA.
Ling
T
T
Tran
H V
HV
Theodorakis
E A
EA
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D004815:Epidermal Growth Factor / Q000037:antagonists & inhibitors; D019906:Nuclear Magnetic Resonance, Biomolecular; D011500:Protein Synthesis Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D000970:Antineoplastic Agents; D011500:Protein Synthesis Inhibitors; D011714:Pyrans; D013141:Spiro Compounds; C068098:reveromycin A; D004815:Epidermal Growth Factor