One-Pot Total Synthesis of Cannabinol via Iodine-Mediated Deconstructive Annulation

被引：25

作者：

Caprioglio, Diego ^{[1
]}

Mattoteia, Daiana ^{[1
]}

Minassi, Alberto ^{[1
]}

Pollastro, Federica ^{[1
]}

Lopatriello, Annalisa ^{[2
]}

Munoz, Eduardo ^{[3
]}

Taglialatela-Scafati, Orazio ^{[2
]}

Appendino, Giovanni ^{[1
]}

机构：

[1] Univ Piemonte Orientale, Dipartimento Sci Farmaco, Largo Donegani 2, I-28100 Novara, Italy

[2] Univ Napoli Federico II, Dipartimento Farm, Via Montesano 49, I-80131 Naples, Italy

[3] Univ Cordoba, Maimonides Biomed Res Inst Cordoba, Avda Menendez Pidal S-N, E-14004 Cordoba, Spain

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 15期

关键词：

CYCLOADDITION; AROMATIZATION; CANNABICYCLOL; MARIJUANA; MECHANISM;

D O I：

10.1021/acs.orglett.9b02258

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The thermal degradation of cannabichromene (CBC, 3) is dominated by cationic reactions and not by the pericyclic rearrangements observed in model compounds. The rationalization of these differences inspired the development of a process that coupled, in an aromatization-driven single operational step, the condensation of citral and alkylresorciniols to homoprenylchromenes and their in situ deconstructive annulation to benzo[c]chromenes. This process was applied to a total synthesis of cannabinol (CBN, 5) and to its molecular editing.

引用

页码：6122 / 6125

页数：4

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