Chapter 31: Q41P (page 1260)
Farnesyl diphosphate is cyclized to sesquiterpene A, which is then converted to the bicyclic product epi-aristolochene. Write a stepwise mechanism for both reactions.
Short Answer
Answer
The mechanism of the reaction
Chapter 31: Q41P (page 1260)
Farnesyl diphosphate is cyclized to sesquiterpene A, which is then converted to the bicyclic product epi-aristolochene. Write a stepwise mechanism for both reactions.
Answer
The mechanism of the reaction
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Get started for free(a) Draw a skeletal structure of the anabolic steroid 4-androstene-3, 17-dione, also called โandro,โ from the following description. Andro contains the tetracyclic steroid with carbonyl groups at C3 and C17, a double bond between C4 and C5, and methyl groups bonded to C10 and C13.
(b) Add wedges and dashed wedges for all stereogenic centers with the following information: the configuration at C10 is R, the configuration at C13 is S, and all substituents at ring fusions are trans to each other.
Draw three-dimensional structures for each alcohol. Label the OH groups as occupying axial or equatorial positions.
a.
b.
c.
d.
Convert the ball-and-stick model of androsterone to (a) a skeletal structure using wedges and dashed wedges around all stereogenic centers; and (b) a three-dimensional representation using chair cyclohexane rings.
androsterone
The biosynthesis of lanosterol from squalene has intrigued chemists since its discovery. It is now possible, for example, to synthesize polycyclic compounds from acyclic or monocyclic precursors by reactions that form several C-C bonds in a single reaction mixture.
Flexibilene is a terpene isolated from Sinulariaflexibilis, a soft coral found in the Indian Ocean. Draw a stepwise mechanism for the formation of flexibilene from farnesyl diphosphate and isopentenyl diphosphate. What is unusual about the cyclization that forms the 15-membered ring of flexibilene?
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