Organic letters

s eco-C/D Ring Analogues of Ergot Alkaloids. Synthesis via Intramolecular Heck and Ring-Closing Metathesis Reactions

AV Kalinin, BA Chauder, S Rakhit, V Snieckus

Index: Kalinin, Alexey V.; Chauder, Brian A.; Rakhit, Suman; Snieckus, Victor Organic Letters, 2003 , vol. 5, # 19 p. 3519 - 3521

Full Text: HTML

Citation Number: 47

Abstract

To test the RCM protocol 2 for the construction of the seco-C/D ring framework 16, the common starting 4-bromoindole 5 was subjected to sequential Stille coupling with allyltributyltin, 18 LAH reduction, and acylation to furnish the 4-allyltryptamine 14 in 42% overall yield (Scheme 3). Treatment with Boc 2 O followed by N-allylation afforded the RCM precursor 15. Using the first-generation catalyst [(PCy 3 ) 2 (Cl) 2 Ru CHPh] 2 in refluxing CH 2 Cl 2 under syringe pump addition ...

Related Articles:

Applications of vinylogous Mannich reactions. Total syntheses of the ergot alkaloids rugulovasines A and B and setoclavine

[Liras; Lynch; Fryer; Vu; Martin Journal of the American Chemical Society, 2001 , vol. 123, # 25 p. 5918 - 5924]

Novel applications of vinylogous Mannich reactions. Total synthesis of rugulovasines A and B

[Martin; Liras Journal of the American Chemical Society, 1993 , vol. 115, # 22 p. 10450 - 10451]

The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halogeno group and a carbon functional group at the 4-position

[Somei; Kizu; Kunimoto; Yamada Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 9 p. 3696 - 3708]

The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halogeno group and a carbon functional group at the 4-position

[Somei; Kizu; Kunimoto; Yamada Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 9 p. 3696 - 3708]

The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halogeno group and a carbon functional group at the 4-position

[Somei; Kizu; Kunimoto; Yamada Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 9 p. 3696 - 3708]

More Articles...