3 stereocenters 8steps synthesis in b−ab−abc construction

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Danylo Hatych Liu Research Group Total Synthesis Presentation 02/10/2021 G.Liu et al. Org. Lett. 2021, 23, 2, 290–295 • isolated from the gorgonian coral Rumphella antipathies • tricyclo[6.3.1.0]dodecane ring system • 3 stereocenters • 8 steps synthesis in B−AB−ABC construction sequence • this synthesis serves as a general platform to concisely access the clovane-type sesquiterpenoids.

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Page 1: 3 stereocenters 8steps synthesis in B−AB−ABC construction

Danylo HatychLiu Research Group

Total Synthesis Presentation02/10/2021

G.Liu et al. Org. Lett. 2021, 23, 2, 290–295

• isolated from the gorgonian coral Rumphella antipathies• tricyclo[6.3.1.0]dodecane ring system• 3 stereocenters• 8 steps synthesis in B−AB−ABC construction sequence• this synthesis serves as a general platform to concisely access

the clovane-type sesquiterpenoids.

Page 2: 3 stereocenters 8steps synthesis in B−AB−ABC construction

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Page 3: 3 stereocenters 8steps synthesis in B−AB−ABC construction

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Retrosynthetic analysis of Rumphellclovane E

Page 4: 3 stereocenters 8steps synthesis in B−AB−ABC construction

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Rh2(esp)2

bis[rhodium(α,α,α’,α’-tetramethyl-1,3-benzenedipropionic acid

From 10 to 11: Rh-catalyzed cyclopropanation

From 9 to 12 : Intramolecular acylation

Page 5: 3 stereocenters 8steps synthesis in B−AB−ABC construction

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From 12 to 8: Michael addition From 8 to 7a/7b: Metal-catalyzed reductive aldol reaction

Fe(acac)3

Page 6: 3 stereocenters 8steps synthesis in B−AB−ABC construction

From 15a/15b to 16: Hydrogenolysis under heterogeneous Catalysis

From 7a/7b to 15a/15b : TBS protection of alcohol

From 16 to 17: Hydrolysis and decarboxylation

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Page 7: 3 stereocenters 8steps synthesis in B−AB−ABC construction

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From 17 to 18: Selective reduction of carbonyl

From 18 to 4: TBS deprotection

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