Synthesis of HKI 0231B.
[reaction: see text] The total synthesis of HKI 0231B (1b) was completed in 12 linear steps and 15.6% overall yield. An unusual anionic cyclization provided access to intermediate 61 and the embedded benz[cd]indol-3-(1H)-one ring system 3. Directed ortho-lithiation in the presence of a ketone followed by formylation and finally acid-catalyzed methanolysis complete the synthesis. Studies directed toward the construction and reactivity of the lactam acetal functionality present in HKI 0231A (1a) are also reported.
Scopton
Alex
A
E. F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Kelly
T Ross
TR
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D000470:Alkaloids; C511503:HKI 0231A; C511501:HKI 0231B; D007211:Indoles