@article {1632,
	title = {A synthetic approach toward nitiol: Construction of two 1,22-dihydroxynitianes},
	journal = {Journal of Organic Chemistry},
	volume = {71},
	number = {11},
	year = {2006},
	note = {ISI Document Delivery No.: 044EATimes Cited: 8Cited Reference Count: 131Wilson, Michael S. Woo, Jacqueline C. S. Dake, Gregory R.},
	month = {May},
	pages = {4237-4245},
	type = {Review},
	abstract = {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.},
	keywords = {1ST TOTAL-SYNTHESIS, ACTIVE, ALKYL BROMIDES, ARYL GRIGNARD-REAGENTS, BETA-SILOXY ALDEHYDES, CARBON BOND FORMATION, IRELAND-CLAISEN REARRANGEMENT, PAUSON-KHAND REACTION, PLAGIOSPIROLIDE-A, TRANSITION-METAL CATALYSIS, ZIRCONIUM-CATALYZED CARBOALUMINATION},
	isbn = {0022-3263},
	url = {<Go to ISI>://000237654000027},
	author = {Wilson, M. S. and Woo, J. C. S. and Dake, G. R.}
}
