Reaction of tricarbonyl(dienal)iron complexes with B-allyldiisopinocampheylborane

Addition of allyldiisopinocampheylborane to racemic (dienal)iron complexes, followed by oxidation, affords diastereomeric (1,4,6-trien-3-ol)iron complexes with moderate to low enantioselectivity. The high enantioselectivity typically observed for this allylborane reagent is attenuated by steric interaction between the Fe(CO)3 group and the chiral isopinocampheyl groups. Further diminution of the enantioselectivity is observed for dienal complexes in which one rotomer predominates

Development of Organoiron Methodology for Preparation of the Polyene Natural Product Macrolactin A

Methodology for the synthesis of the C7–C13 segment (19) and C14–C24 segment (41) of macrolactin A have been developed. Dicarbonyl(methyl 7-nitro-2E,4Z-heptadienoate)triphenylphosphineiron (19) is prepared by nucleophilic addition to a (1-methoxycarbonylpentadienyl)iron cation. The C23 stereocenter of 41 is established by introduction of a C20 stereocenter, chirality transfer from C20 to C23 followed by (diene)iron mediated selective ionic reduction of the C20 hydroxyl. The C15 stereocenter may be established by nitrile oxide–olefin cyclocondensation

Enantioselective Synthesis of the C11-C24 Segment of Macrolactin a via Organoiron Methodology

The enantioselective synthesis of the Fe(CO)3 completed C11-C24 segment of macrolactin A has been accomplished from rac-(methyl 6-oxo-2,4-hexadienoate)Fe(CO)3 in 11 steps (\u3e50% ee)

A stereoselective synthesis of 8(R) and 8(S),11(R),12(S)-trihydroxyeicosa-5(Z),9(E),14(Z)-trienoic acid from 2-deoxy-D-ribose

A stereoselective synthesis of stereoisomers of the title compound from 2-deoxy-D-Ribose using reductive elimination protocol<SUP>1</SUP> as the key step is described. Stereoselective synthesis of Trioxilin A<SUB>3</SUB> from 2-deoxy-D-Ribose is described