Guggul is an herbal extract from the resin of the mukul myrrh tree, and it shows
Chapter 14, Problem 14.66(choose chapter or problem)
Guggul is an herbal extract from the resin of the mukul myrrh tree, and it shows potential for treating high cholesterol. In a recent synthesis of (+)-myrrhanol A (a compound present in guggul), compound 1 was treated with MCPBA, followed by LAH to afford compound 2 as the only diastereomer detected (J. Org. Chem. 2009, 74, 61516156). Draw a mechanism for the transformation of 1 to 2 and explain the stereochemical outcome with respect to the newly formed chirality center. Your explanation should include (i) a bond-line drawing that clearly shows the chair conformation adopted by each six-membered ring in the trans-decalin system and (ii) a Newman projection that clearly shows the source of the observed stereochemical preference. TMSO H OH TMSO H OH 1) MCPBA OH 2) LAH 3) H2O 1 2
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