The Journal of Organic Chemistry

Regiocontrolled synthesis of hydroxyphthalides. Synthesis of (.+-.)-isoochracinic acid and a zealeranone intermediate

BM Trost, GT Rivers, JM Gold

Index: Trost, Barry M.; Rivers, Gordon T.; Gold, Jeffrey M. Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1835 - 1838

Full Text: HTML

Citation Number: 58

Abstract

Metalation of 3-methoxy-and 3, 5-dimethoxybenzyl alcohol followed by quenching with COz provided the phthalides. Bromination and solvolysis generated 7-methoxy-and 5, 7- dimethoxyphthalaldehydic acid in a fully regiocontrolled reaction. The former served as an intermediate in the synthesis of isoochracinic acid, a toxic metabolite from a parasite responsible for black spot disease of Japanese pears, in 44% overall yield from 3- ...

Related Articles:

Regiospecific synthesis of 3-(2, 6-dihydroxyphenyl) phthalides: application to the synthesis of isopestacin and cryphonectric acid

[Mal, Dipakranjan; Pahari, Pallab; De, Saroj Ranjan Tetrahedron, 2007 , vol. 63, # 47 p. 11781 - 11792]

Efficient synthesis of anacardic acid analogues and their antibacterial activities

[Mamidyala, Sreeman K.; Ramu, Soumya; Huang, Johnny X.; Robertson, Avril A.B.; Cooper, Matthew A. Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 6 p. 1667 - 1670]

Synthesis of a regioisomeric analogue of the 3C-protease inhibitor thysanone via a Hauser annulation strategy

[Brimble, Margaret A.; Houghton, Scott I.; Woodgate, Paul D. Tetrahedron, 2007 , vol. 63, # 4 p. 880 - 887]

Synthesis of functionalized hydroxyphthalides and their conversion to 3-cyano-1 (3H)-isobenzofuranones. The Diels-Alder reaction of methyl 4, 4-diethoxybutynoate …

[Freskos, John N.; Morrow, Gary W.; Swenton, John S. Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 805 - 810]

Synthesis of functionalized hydroxyphthalides and their conversion to 3-cyano-1 (3H)-isobenzofuranones. The Diels-Alder reaction of methyl 4, 4-diethoxybutynoate …

[Freskos, John N.; Morrow, Gary W.; Swenton, John S. Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 805 - 810]

More Articles...