1234580-28-9Relevant articles and documents
A novel asymmetric synthesis of the core octadienoic acid unit of cryptophycins from (R)-2,3- O -cyclohexylideneglyceraldehyde
Goswami, Dibakar,Sur, Payel,Chattopadhyay, Angshuman,Sharma, Anubha,Chattopadhyay, Subrata
, p. 1626 - 1632 (2011)
A facile asymmetric synthesis of the octadienoic acid unit of cryptophycins was developed starting from (R)-2,3-O-cyclohexylideneglyceraldehyde. The key steps of the synthesis are the stereocontrolled generation of the required asymmetric centers through
Crotylation of (R)-2,3-O-cyclohexylideneglyceraldehyde: a simple synthesis of (+)-trans-oak lactone
Chattopadhyay, Angshuman,Goswami, Dibakar,Dhotare, Bhaskar
supporting information; scheme or table, p. 3893 - 3896 (2010/08/20)
Crotylations of (R)-2,3-cyclohexylideneglyceraldehyde (1) were utilized in a simple synthesis of trans-oak lactone (I), a representative example of chiral β,γ-disubstituted-γ-butyrolactones. In this endeavor, crotylations of 1 in THF mediated with four low valent metals were studied. All these reactions took place efficiently producing 2 in good yields but with varied stereoselectivities. Each reaction produced the corresponding secondary alcohol adduct 2b and 2c predominantly with diastereoisomer 2a only in trace amounts. Among these four reactions, only Sn-mediated addition yielded 2b as the major products. Later, 2c was converted into 2d through oxidation-reduction. Finally, 2c was transformed into trans-oak lactone I in a few steps. Following this route, 2a, 2b, and 2d would produce other stereoisomers of oak lactone.
