1971

DOI: 10.1021/jo00805a027

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Cyclization of cis- and trans-2-(2-methoxycyclohexyl)ethanol to cis- and trans-perhydrobenzofurans

Robert J. Gargiulo¹,

Yasushi Yamämoto²,

D. S. Tarbell³

Abstract: We have reported2 that compounds of type 1 undergo cyclization with tosyl chloride-pyridine to form perhydrobenzofurans 2, with loss of a methoxyl group. This reaction, which we first observed in degradations of the antibiotic fumagillin,3 involves a methoxonium ion intermediate.4

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Cited by 9 publications

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Intramolecular Photocycloaddition ofN-Alkenyl Substituted Maleimides: A Potential Tool for the Rapid Construction of Perhydroazaazulene Alkaloids

Booker‐Milburn

¹

,

²

,

³

et al. 2001

Eur. J. Org. Chem.

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UV irradiation of a number of N-alkenyl-substituted maleimide derivatives leads to the formation of complex perhydroazaazulenes in excellent yields. The overall process can be considered as a formal intramolecular [5+2] cycloaddition. Substrates were prepared by Mitsunobu coupling of the appropriate alkenols with various maleimides. Methyl substitution of the alkenyl side chain gave the cycloadducts 13a−g in good yields, with moderate to high stereoselectivity being Scheme 1 [a]

Intramolecular Photocycloaddition ofN-Alkenyl Substituted Maleimides: A Potential Tool for the Rapid Construction of Perhydroazaazulene Alkaloids

Booker‐Milburn

¹

,

²

,

³

et al. 2001

Eur. J. Org. Chem.

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UV irradiation of a number of N-alkenyl-substituted maleimide derivatives leads to the formation of complex perhydroazaazulenes in excellent yields. The overall process can be considered as a formal intramolecular [5+2] cycloaddition. Substrates were prepared by Mitsunobu coupling of the appropriate alkenols with various maleimides. Methyl substitution of the alkenyl side chain gave the cycloadducts 13a−g in good yields, with moderate to high stereoselectivity being Scheme 1 [a]

Hydrogenated Benzofurans

1974

Chemistry of Heterocyclic Compounds: A Series of Monographs

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No abstract

ChemInform Abstract: DIE CYCLISIERUNG VON CIS‐ UND TRANS‐2‐(2‐METHOXYCYCLOHEXYL)‐AETHANOL ZU CIS‐ UND TRANS‐PERHYDROBENZOFURANEN

1971

Chemischer Informationsdienst. Organische Chemie

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Die cis‐2‐(2‐Methoxycyclohexyl)‐äthanole (Ia)‐(Ic) liefern mit Tosylchlorid/ Pyridin die entsprechenden cyclischen Äther (IIa)‐(IIc).

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