Guggul is an herbal extract from the resin of the mukul myrrh tree, and it shows

Chapter 14, Problem 14.66

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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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