Synthesis of Hirsutene

Structure of Hirsutene

C15H24

Principal investigator	Kuniaki Tatsuta
Publication year	1979
Synthesis type	Formal
Number of steps	20 (linear)
References	J. Am. Chem. Soc. 1979, 101, 6116.

Part 1 of 1

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Br2

THF

10 °C

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(CH2OH)2, TsOH

PhH

Reflux

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KOt-Bu

DMSO

15 °C

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Bz2O2, NBS

CCl4

Reflux

See the Wohl-Ziegler Reaction

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AgOAc

Et2O

RT, 54% (5 steps)

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+

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hν

Cyclohexane

RT, 2.5 d

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NaBH4

MeOH

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i-Pr2NEt, MeOCH2Cl

RT, 5 h

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NaOMe

MeOH

RT, 24 h, 74% (3 steps)

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TsCl

Pyr

RT, 4 h, 82%

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K2CO3

Sealed tube

Acetone, H2O

85 °C, 24 h, 90%

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Zn, NaI

DMF, H2O

130 °C, 2 d

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H2SO4

Acetone, H2O

RT, 4 h, 56% (2 steps)

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H2, Pd

3 atm

MeOH

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LiAlH4

THF

87% (2 steps)

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"No experimental details were reported."

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AIBN, n-Bu3SnH

PhH

90%

See the Barton-McCombie Reaction

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H2SO4

Acetone, H2O

50 °C

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HCrO3Cl.Pyr

CH2Cl2

86% (2 steps)

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Remaining...

70% (1 step)

"See: <i>Tetrahedron Lett. 1976, 17, 195."

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