The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid

• Ishmael B. Masesane,
• Andrei S. Batsanov,
• Judith A. K. Howard,
• Raju Mondal and
• Patrick G. Steel

Beilstein J. Org. Chem. 2006, 2, No. 9, doi:10.1186/1860-5397-2-9

• oxanorbornene adduct derived from the Diels-Alder reaction of ethyl (E)-3-nitroacrylate and furan provides a versatile template for the stereoselective synthesis of hydroxylated derivatives of 2-aminocyclohexanecarboxylic acid (ACHC). Introduction In recent years there has been a surge of interest in cyclic β

• describe the stereoselective synthesis of further novel hydroxylated derivatives of ACHC using the exo nitro oxanorbornene adduct as the template. The basis of our approach to these poly hydroxylated cyclohexane β-amino acids was the recognition that the bicyclic oxanorbornene cycloadduct, derived from the

Synthesis of 2,6-trans- disubstituted 5,6-dihydropyrans from (Z)-1,5-syn-endiols

• Eric M. Flamme and
• William R. Roush

Beilstein J. Org. Chem. 2005, 1, No. 7, doi:10.1186/1860-5397-1-7

• -dihydropyrans. Furthermore, there are only limited reports describing the stereoselective synthesis of related tetrahydropyrans through cyclodehydration of enantiopure 1,5-diols substrates.[17] The challenge of synthesizing dihydropyrans 3 or ent-3 from 1,5-diols such as 2 lies in the differentiation of the two