TY - JOUR

T1 - Efficient Synthesis of the N-(buta-2,3-dienyl)carboxamide of Isopimaric Acid and the Potential of This Compound towards Heterocyclic Derivatives of Diterpenoids

AU - Gromova, Marya A.

AU - Kharitonov, Yurii V.

AU - Bagryanskaya, Irina Yu

AU - Shults, Elvira E.

PY - 2018/11/1

Y1 - 2018/11/1

N2 - The N-(2,3-butadienyl)carboxamide of isopimaric acid, that is, compound 3, was prepared through a two-step synthetic procedure starting from the natural diterpene isopimaric acid. The Pd-catalyzed cross-coupling and subsequent cyclization of terpenoid allene 3 with several aryl iodides and aryl bromides gave access to optically active diterpenoid–oxazoline derivatives in good to excellent yields. The functional group tolerance in the aryl iodides was demonstrated by several examples, including substrates with additional N-tert-butoxycarbonyl-protected amino, hydroxy, and carboxy substituents in the ortho position. The cross-coupling–cyclization reaction of those compounds with allene 3 proceeded selectively with the formation of cyclization products on the substituent in the aromatic ring. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid and several heterocycles.

AB - The N-(2,3-butadienyl)carboxamide of isopimaric acid, that is, compound 3, was prepared through a two-step synthetic procedure starting from the natural diterpene isopimaric acid. The Pd-catalyzed cross-coupling and subsequent cyclization of terpenoid allene 3 with several aryl iodides and aryl bromides gave access to optically active diterpenoid–oxazoline derivatives in good to excellent yields. The functional group tolerance in the aryl iodides was demonstrated by several examples, including substrates with additional N-tert-butoxycarbonyl-protected amino, hydroxy, and carboxy substituents in the ortho position. The cross-coupling–cyclization reaction of those compounds with allene 3 proceeded selectively with the formation of cyclization products on the substituent in the aromatic ring. This transformation opens a potential route to the synthesis of hybrid compounds containing a tricyclic diterpenoid and several heterocycles.

KW - chromenes

KW - cross-coupling

KW - cyclization

KW - heterocycles

KW - terpenoids

UR - http://www.scopus.com/inward/record.url?scp=85057541553&partnerID=8YFLogxK

U2 - 10.1002/open.201800205

DO - 10.1002/open.201800205

M3 - Article

C2 - 30460170

AN - SCOPUS:85057541553

VL - 7

SP - 890

EP - 901

JO - ChemistryOpen

JF - ChemistryOpen

SN - 2191-1363

IS - 11

ER -