vitamin B12 - 2024 ACF Winter

Question

Answer the following about Robert Woodward’s contributions to total syntheses, for 10 points each.

[10e] Woodward led the Harvard team, which joined forces with Albert Eschenmoser’s ETH team, in the total synthesis of this compound. This largest B vitamin’s central corrin ring contains a cobalt atom.

ANSWER: vitamin B12 [or cobalamin]

[10m] The first step of Woodward’s classic strychnine (“STRICK-neen”) synthesis begins with a Fischer indole synthesis, involving a phenyl derivative of this compound. The Olin Raschig process produces this compound found in rocket fuels.

ANSWER: hydrazine [or N2H4; accept phenylhydrazine]

[10h] Woodward and Doering’s 1944 total synthesis of quinine stood until this chemist published a stereoselective pathway in 2001. Carbonyls are selectively alkylated in this chemist’s namesake enamine synthesis.

ANSWER: Gilbert Stork [accept Stork enamine synthesis]

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Summary


2024 ACF Winter at Lehigh	2024-11-16	Y	7	12.86	100%	29%	0%
2024 ACF Winter at Northwestern	2024-11-16	Y	9	12.22	56%	56%	11%
2024 ACF Winter at Ohio State	2024-11-16	Y	9	6.67	22%	33%	11%
2024 ACF Winter at Online	2024-11-16	Y	7	15.71	86%	71%	0%
2024 ACF Winter at Central Florida	2024-11-16	Y	4	17.50	100%	50%	25%
2024 ACF Winter at Oxford	2024-11-16	Y	8	11.25	63%	50%	0%
2024 Booster Shot (Columbia)	02/23/2024	N	6	20.00	100%	67%	33%
2024 Booster Shot (Great Lakes)	03/09/2024	N	6	15.00	100%	50%	0%
2024 Booster Shot (Vanderbilt)	03/02/2024	N	4	15.00	100%	25%	25%
2024 Booster Shot (WUSTL)	03/09/2024	N	3	13.33	100%	33%	0%
2024 Booster Shot (Waterloo)	02/23/2024	N	4	20.00	100%	100%	0%

Data


Johns Hopkins B	Rutgers A	10	10	0	20
Penn A	Penn B	10	0	0	10
Penn State A	Columbia A	10	0	0	10
Penn State B	Rutgers C	10	10	0	20
Purdue A	Indiana A	10	10	0	20
UIUC D	Miami	0	10	0	10
Northwestern A	Notre Dame	10	10	0	20
SIUE A	Purdue B	0	0	0	0
Purdue C	WashU C	0	0	0	0
Indiana B	UChicago D	0	0	0	0
UIUC A	UChicago C	10	10	0	20
WashU B	UIUC B	10	10	0	20
UChicago B	UIUC C	10	0	10	20
Rowan A	Bard A	10	0	0	10
Columbia B	Johns Hopkins A	10	0	0	10
Haverford A	Princeton A	10	0	0	10
CWRU A	Ohio State C	0	10	0	10
CWRU C	Kenyon A	0	0	0	0
CWRU B	Michigan C	0	0	0	0
Michigan D	Michigan State C	10	0	0	10
Michigan State A	Pitt A	0	10	0	10
Pitt B	Michigan State B	0	0	0	0
Ohio State A	Michigan A	10	0	10	20
Michigan B	Ohio State B	0	10	0	10
CWRU D	Kenyon B	0	0	0	0
Missouri	Iowa	10	10	0	20
McGill E	Oregon State	10	0	0	10
Texas C	Colorado College	0	10	0	10
Vassar A	Texas A	10	10	0	20
Vassar B	Texas D	10	0	0	10
WUSTL A	NYU B	10	10	0	20
Mississippi State	Central Oklahoma	10	10	0	20
Florida Tech A	UF D	10	0	0	10
UCF A	Florida State University A	10	10	0	20
UF B	UCF B	10	10	10	30
UF E	UF F	10	0	0	10
Birmingham	Durham	10	0	0	10
Cambridge A	Bristol A	10	10	0	20
Cambridge B	Imperial A	0	10	0	10
Cambridge C	Manchester	0	10	0	10
Southampton A	Cambridge D	0	0	0	0
Imperial B	Warwick A	10	0	0	10
Oxford A	LSE A	10	10	0	20
Southampton B	Oxford B	10	0	0	10