Strategic approaches to the synthesis of pyrrolizidine and indolizidine alkaloids

Strategic approaches to the synthesis of pyrrolizidine and indolizidine alkaloids Review

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2020, Volume: 76, Number: 14, Article number : 131031, Pages count : DOI: 10.1016/j.tet.2020.131031

Authors

Ratmanova Nina K. ¹ , Andreev Ivan A. ^1,2 , Leontiev Alexandre V. ³ , Momotova Daria ³ , Novoselov Anton M. ⁴ , Ivanova Olga A. ^4,2 , Trushkov Igor V. ^1,2

Affiliations

1	Laboratory of Chemical Synthesis, Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow, 117997, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow, 119991, Russian Federation
3	Institute of Mathematics & Natural Sciences, North-Caucasus Federal University, Pushkin St. 1, Stavropol, 355000, Russian Federation
4	Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1-3, Moscow, 119991, Russian Federation

The principal methods for the synthesis of pyrrolizidine and indolizidine alkaloids and their unnatural analogs are described. Six main “strategic” approaches in regard to a key step forming azabicyclic skeleton are identified. Namely, these are: 1) hydrogenation of the corresponding heteroaromatic compounds; 2) various condensations of carbonyl compounds and their surrogates; 3) cycloaddition reactions; 4) sigmatropic shifts and other rearrangements; 5) transition metal-mediated cyclizations (including the ring-closing alkene metathesis); and 6) radical processes. Such important issues, as retrosynthetic analysis, chiral pool synthesis, and chiral auxiliaries, are also discussed.

Ratmanova N.K. , Andreev I.A. , Leontiev A.V. , Momotova D. , Novoselov A.M. , Ivanova O.A. , Trushkov I.V.
Strategic approaches to the synthesis of pyrrolizidine and indolizidine alkaloids
Tetrahedron. 2020. V.76. N14. 131031 . DOI: 10.1016/j.tet.2020.131031 WOS Scopus OpenAlex

Web of science:	WOS:000525713100004
Scopus:	2-s2.0-85080091744
OpenAlex:	W3005918886

DB	Citing
OpenAlex	60
Scopus	51
Web of science	49