132352-53-5Relevant academic research and scientific papers
A synthetic approach toward nitiol: Construction of two 1,22-dihydroxynitianes
Wilson, Michael S.,Woo, Jacqueline C. S.,Dake, Gregory R.
, p. 4237 - 4245 (2006)
Synthetic work toward the total synthesis of nitiol has culminated in the construction of two epimeric hydroxylated derivatives, the 1,22- dihydroxynitianes. Key stereodefining steps in the construction of the A-ring fragment (13) were the use of a siloxy-epoxide rearrangement reaction, a Pauson-Khand reaction, a Norrish 1 photochemical cleavage reaction, and a highly regio- and stereoselective hydrostannylation reaction of an ynoate. The stereochemistry of the synthetically challenging C-ring fragment (20) was established using an Ireland-Claisen reaction and a Grubbs ring-closing metathesis process as key steps. The 12-membered B-ring of the nitiane skeleton was constructed using a copper-promoted Stille cross-coupling and a Kishi-Hiyama-Nozaki carbonyl addition reaction. Unfortunately, the carbonyl addition reaction produced hydroxyl functionality that could not be selectively removed. Consequently, a synthesis of epimeric 1,22-dihydroxynitianes, which are compounds that are structural hybrids of two natural products, nitiol and variculanol, was completed.
AN EFFECTIVE, PRACTICAL METHOD FOR THE SYNTHESIS OF CHIRAL PROPARGYL ALCOHOLS
Yadav, J. S.,Deshpande, Prasad K.,Sharma, G. V. M.
, p. 7033 - 7046 (2007/10/02)
The preparation of chiral propargyl alcohols (2) is described by LiNH2 or LDA induced double elimination of chiral epoxychlorides (4), derived from their corresponding epoxyalcohols (3) which are available easily by Sharpless asymmetric epoxidation of the primary allyl alcohols.Whereas, use of stoichiometric amount of base on 4 provides chirally enriched trans-1-chlorovinyl alcohols (14).
