Synthetic Studies Directed Toward Streptenol D: Enantioselective Preparation of the 3,5-diacetoxy-6\u3cem\u3eE\u3c/em\u3e,8\u3cem\u3eE\u3c/em\u3e-decadiene Segment

The enantioselective preparation of 2-(3′R,5′R-diacetoxy-6E,8E-decadienyl)-1,3-dioxane, (+)-13, is described. This synthesis of the skeleton of streptenol D utilizes the ability of a diene-complexed (tricarbonyl)iron unit to serve as a protecting and stereodirecting functionality

Asymmetric Synthesis of Streptenol D : Oxidation and Reduction of (dienol)iron Complexes

The use of transition organometallic complexes as reagents for the synthesis of complex organic molecules has been under intensive growth and development for several decades, and many organic transformations of profound synthetic potential has been achieved. Particularly, the use of organoiron complexes has been recognized as a powerful tool in the synthetic methodology due to their ability to react with nucleophiles and electrophiles in a stereoselective fashion. The use of NMO as a chemoselective, metal mediated oxidizing agent will be discussed

Chemoselective, Metal-Mediated Oxidation of (dienol)iron Complexes with N-methylmorpholine N-oxide

The oxidation of (dienol)iron complexes to the corresponding (dienal)iron complexes by amine N-oxides is reported. This oxidation is selective for a hydroxyl group adjacent to the complexed diene. The oxidation of (dienol)iron complexes to the corresponding (dienaliron complexes by amine N-oxides is reported. The oxidation is selective for a hydroxyl group adjacent to the complexed diene

Crystal and Molecular Structure of 569-1569-1569-1, C\u3csub\u3e12\u3c/sub\u3eH\u3csub\u3e16\u3c/sub\u3eO\u3csub\u3e5\u3c/sub\u3eFe

The relative stereochemistry of the tricarbonyl(5,6,7,8-η4-5,7-nonadien-2,4-diol)iron was revealed to be (2S*,4S*,5S*) by single crystal X-ray diffraction analysis

Remote Diastereoselective Control via Organoiron Methodology: Stereoselective Preparation of 4,6-, 5,7- and 6,8-dien-2-ol (tricarbonyl) Iron Complexes

The diastereoselective preparation of 2,3-, 2,4- and 2,5-diol iron complexes was accomplished in the following fashion: (2,4,6-octatriene)Fe(CO)3undergoes diastereoselective osmylation to provide (4,6-octadien-2,3-diol)Fe(CO)3; (4-hydroxy-5,7-nonadien-2-one)Fe(CO)3 may be reduced in a diastereoselective fashion to give mixtures predominating in either the syn- or anti-(5,7-nonadien-2,4-diol)Fe(CO)3; and diastereospecific addition of MeTi(OiPr)3 to the lactol of (5-hydroxy-6,8-decadienal)Fe(CO)3 gives (6,8-decadien-2,5-diol)Fe(CO)3. In each of the cases noted above, the hydroxyl group adjacent to the (diene)Fe(CO)3 group may be removed via ionic hydrogenation. The ionization of this hydroxyl is rationalized on the basis of the intermediacy of a transoid (pentadienyl)Fe(CO)3 cation species

Alkylation of Tricarbonyl(diene)iron Complexes: Model Studies for the Preparation of Protomycinolide IV

The alkylation of (4,6-heptadien-3-one)- and (methyl 3,5-hexadienoate)Fe(CO)3 (1 and 2) were examined (0–42% de and 69–92% de respectively). Optically active (methyl 3,5-hexadienoate)Fe(CO)3 (−)-2 was prepared by resolution of the corresponding carboxylic acid complex with α-methylbenzylamine. The alkylation of (4,6-heptadien-3-one)-Fe(CO)3 (1, 0–42% de) and (methyl 3,5-hexadienoate)Fe(CO)3 (2, 70–92% de) were examined